Benzamide compounds and their use as herbicides

ABSTRACT

The invention relates to a compound of formula I, 
                         
an N-oxide or an agriculturally suitable salt thereof, wherein the variables are as defined in the specification, and their use as herbicides.

This application is a National Stage application of International Application No. PCT/EP2016/078609, filed Nov. 24, 2016. This application also claims priority under 35 U.S.C. § 119 to European Patent Application No. 15200842.1, filed Dec. 17, 2015, and European Patent Application No. 16193193.6, filed Oct. 11, 2016.

The present invention relates to benzamide compounds and compositions comprising the same. The invention also relates to the use of the benzamide compounds or the corresponding compositions for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying the benzamide compounds or the corresponding compositions.

For the purpose of controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides that have high activities and selectivities together with a substantial lack of toxicity for humans and animals.

WO 2013/072300 and patent EP 0,173,657 B1 describe oxadiazole compounds and their use as herbicides.

WO 2013/083859 describes substituted N-(tetrazol-5-yl)- and N-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides.

WO 2013/092834 describes substituted tetrazol compounds and their use as herbicides wherein R⁵ is H.

The compounds of the prior art often suffer form insufficient herbicidal activity, in particular at low application rates, and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.

Accordingly, it is an object of the present invention to provide further benzamide compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants. The benzamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.

These and further objectives are achieved by the compounds of formula I, as defined below, their N-oxides and their agriculturally suitable salts.

It has been found that the above objectives can be achieved by compounds of the present invention, as defined below, including their N-oxides and their salts, in particular their agriculturally suitable salts.

Therefore, the present invention relates to a compound of formula I,

an N-oxide or an agriculturally suitable salt thereof,

wherein

-   -   Q is Q¹ or Q² or Q³ or Q⁴,

-   -   R¹ is selected from the group consisting of halogen,         C₁-C₈-alkyl, C₁-C₈-haloalkyl, nitro, C₁-C₄-alkoxy-C₁-C₄-alkyl,         cyano-Z¹, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl-Z¹,         C₂-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₈-alkoxy,         C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹,         R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where         heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic         or 8-, 9- or 10-membered bicyclic saturated, partially         unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4         heteroatoms as ring members, which are selected from the group         consisting of O, N and S, where the cyclic groups in phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         groups R¹¹, which are identical or different;     -   R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²—;     -   R³ is selected from the group consisting of hydrogen, halogen,         hydroxy-Z², nitro, C₁-C₄-nitroalkyl, cyano, C₁-C₄-cyanoalkyl,         C₁-C₆-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl-Z²,         C₃-C₁₀-cycloalkoxy-Z², where the C₃-C₁₀-cycloalkyl groups in the         two aforementioned radicals are unsubstituted or partially or         completely halogenated, C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl,         C₃-C₈-haloalkynyl, C₁-C₈-alkoxy-Z², C₁-C₈-haloalkoxy-Z²,         C₃-C₁₀-cycloalkyl-C₁-C₂-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z²,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z², C₂-C₈-alkenyloxy-Z²,         C₂-C₈-alkynyloxy-Z², C₂-C₈-haloalkenyloxy-Z²,         C₃-C₈-haloalkynyloxy-Z², C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z²,         (tri-C₁-C₄-alkyl)silyl-Z², R^(2b)—S(O)_(k)—Z², R^(2c)—C(═O)—Z²,         R^(2d)O—C(═O)—Z², R^(2d)O—N═CH—Z², R^(2e)R^(2f)N—C(═O)—Z²,         R^(2g)R^(2h)N—Z², phenyl-Z^(2a), heterocyclyl-Z^(2a), where         heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9-         or 10-membered bicyclic saturated, partially unsaturated or         aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as         ring members, which are selected from the group consisting of O,         N and S, where the cyclic groups in phenyl-Z^(2a) and         heterocy-clyl-Z^(2a) are unsubstituted or substituted by 1, 2, 3         or 4 groups R²¹, which are identical or different, rhodano,         C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl,         C₃-C₆-cycloalkenyl-C₁-C₆-alkyl,         C₃-C₆-halocycloalkenyl-C₁-C₆-alkyl, OC(O)R²², OC(O)OR²⁵,         OC(O)N(R²²)₂, OSO₂R²⁵, SO₂OR²², SO₂N(R²²)₂, SO₂N(R²²)C(O)R²²,         SO₂N(R²²)C(O)OR²⁵, SO₂N(R²²)C(O)N(R²²)₂, N(R²²)C(O)OR²⁵,         N(R²²)C(O)N(R²²)₂, N(R²²)S(O)₂OR²², N(R²²)S(O)₂N(R²²)₂,         C(O)N(R²²)OR²², C(O)N(R²²)N(R²²)₂, C(O)N(R²²)C(O)R²²,         C(O)N(R²²)C(O)OR²⁵, C(O)N(R²²)C(O)N(R²²)₂, C(O)N(R²²)SO₂R²⁵,         C(O)N(R²²)SO₂OR²², C(O)N(R²²)SO₂N(R²²)₂, P(O)(OH)₂,         P(O)(O—C₁-C₄-alkyl)₂, C₁-C₆-alkyl-OC(O)R²²,         C₁-C₆-alkyl-OC(O)OR²⁵, C₁-C₆-alkyl-OC(O)N(R²²)₂,         C₁-C₆-alkyl-OSO₂R²⁵, C₁-C₆-alkyl-SO₂OR²²,         C₁-C₆-alkyl-SO₂N(R²²)₂, C₁-C₆-alkyl-SO₂N(R²²)C(O)R²²,         C₁-C₆-alkyl-SO₂N(R²²)C(O)OR²⁵, C₁-C₆-alkyl-SO₂N(R²²)C(O)N(R²²)₂,         C₁-C₆-alkyl-N(R²²)C(O)OR²⁵, C₁-C₆-alkyl-N(R²²)C(O)N(R²²)₂,         C₁-C₆-alkyl-N(R²²)S(O)₂OR²², C₁-C₆-alkyl-N(R²²)S(O)₂N(R²²)₂,         C₁-C₆-alkyl-C(O)N(R²²)OR²², C₁-C₆-alkyl-C(O)N(R²²)N(R²²)₂,         C₁-C₆-alkyl-C(O)N(R²²)C(O)R²², C₁-C₆-alkyl-C(O)N(R²²)C(O)OR²⁵,         C₁-C₆-alkyl-C(O)N(R²²)C(O)N(R²²)₂, C₁-C₆-alkyl-C(O)N(R²²)SO₂R²⁵,         C₁-C₆-alkyl-C(O)N(R²²)SO₂OR²², C₁-C₆-alkyl-C(O)N(R²²)SO₂N(R²²)₂,         C₁-C₆-alkyl-P(O)(OH)₂ and C₁-C₆-alkyl-P(O)(O—C₁-C₄-alkyl)₂;     -   R⁴ is selected from the group consisting of hydrogen, halogen,         C₁-C₈-alkyl, cyano-Z¹, nitro, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₂-C₈-alkenyl,         C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino,         C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k),         C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹,         R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where         heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic         or 8-, 9- or 10-membered bicyclic saturated, partially         unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4         heteroatoms as ring members, which are selected from the group         consisting of O, N and S, where the cyclic groups in phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         groups R¹¹, which are identical or different;     -   R⁵ is selected from the group consisting of halogen, cyano-Z¹,         nitro, C₁-C₈-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₂-C₈-alkenyl,         C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino,         C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k),         C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹,         R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where         heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic         or 8-, 9- or 10-membered bicyclic saturated, partially         unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4         heteroatoms as ring members, which are selected from the group         consisting of O, N and S, where the cyclic groups in phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         groups R¹¹, which are identical or different;     -   R⁶ is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,         where the C₃-C₇-cycloalkyl groups in the two aforementioned         radicals are unsubstituted or partially or completely         halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, R^(b)—S(O)_(n)—C₁-C₃-alkyl,         R^(c)—C(═O)—C₁-C₃-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl,         R^(e)R^(f)N—C(═O)—C₁-C₃-alkyl, R^(g)R^(h)N—C₁-C₃-alkyl, phenyl-Z         and heterocyclyl-Z, where heterocyclyl is a 5- or 6-membered         monocyclic or 8-, 9- or 10-membered bicyclic saturated,         partially unsaturated or aromatic heterocycle, which contains 1,         2, 3 or 4 heteroatoms as ring members, which are selected from         the group consisting of O, N and S, where phenyl and         heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4         groups which are identical or different;     -   R′, R¹¹, R²¹ independently of each other are selected from the         group consisting of halogen, NO₂, CN, C₁-C₆-alkyl,         C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,         C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₃-C₇-cycloalkoxy and         C₁-C₆-haloalkyloxy, or two radicals R¹¹ or R²¹ bound to the same         carbon atom together may form a group ═O;     -   Z, Z¹, Z² independently of each other are selected from the         group consisting of a covalent bond and C₁-C₄-alkanediyl;     -   Z^(2a) is selected from the group consisting of a covalent bond,         C₁-C₄-alkanediyl, O—C₁-C₄-alkanediyl, C₁-C₄-alkanediyl-O and         C₁-C₄-alkanediyl-O—C₁-C₄-alkanediyl;     -   R^(b), R^(1b), R^(2b) independently of each other are selected         from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl and heterocyclyl, where         heterocyclyl is a 5- or 6-membered monocyclic saturated,         partially unsaturated or aromatic heterocycle, which contains 1,         2, 3 or 4 heteroatoms as ring members, which are selected from         the group consisting of O, N and S, where phenyl and         heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4         groups, which are identical or different and selected from the         group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(c), R^(2c) independently of each other are selected from the         group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl,         C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl,         C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl,         C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where         heterocyclyl is a 5- or 6-membered monocyclic saturated,         partially unsaturated or aromatic heterocycle, which contains 1,         2, 3 or 4 heteroatoms as ring members, which are selected from         the group consisting of O, N and S, where phenyl, benzyl and         heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4         groups, which are identical or different and selected from the         group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(d), R^(2d) independently of each other are selected from the         group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl,         C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl,         C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl,         C₁-C₆-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are         unsubstituted or substituted by 1, 2, 3 or 4 groups, which are         identical or different and selected from the group consisting of         halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-haloalkoxy;     -   R^(2c), R^(2d) together with the nitrogen atom, to which they         are bound may form a 4, -5-, 6- or 7-membered, saturated or         unsaturated cyclic radical, which may carry as a ring member a         further heteroatom selected from O, S and N and which is         unsubstituted or may carry 1, 2, 3 or 4 groups, which are         identical or different and selected from the group consisting of         halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-haloalkoxy;     -   R^(e), R^(f) independently of each other are selected from the         group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₁-C₆-haloalkyl,         C₂-C₆-alkenylene, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,         C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl,         where phenyl and benzyl are unsubstituted or substituted by 1,         2, 3 or 4 groups, which are identical or different and selected         from the group consisting of halogen, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or     -   R^(e), R^(f) together with the nitrogen atom, to which they are         bound may form a 5-, 6- or 7-membered, saturated or unsaturated         N-bound heterocyclic radical, which may carry as a ring member a         further heteroatom selected from O, S and N and which is         unsubstituted or may carry 1, 2, 3 or 4 groups, which are         identical or different and selected from the group consisting of         halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-haloalkoxy;     -   R^(2e), R^(2f) independently of each other have the meanings         given for R^(e), R^(f);     -   R^(g) is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,         where the C₃-C₇-cycloalkyl groups in the two aforementioned         radicals are unsubstituted or partially or completely         halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenylene,         C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl,         C₁-C₄-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl         are unsubstituted or substituted by 1, 2, 3 or 4 groups, which         are identical or different and selected from the group         consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(h) is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,         where the C₃-C₇-cycloalkyl groups in the two aforementioned         radicals are unsubstituted or partially or completely         halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, a radical C(═O)—R^(k),         phenyl and benzyl, where phenyl and benzyl are unsubstituted or         substituted by 1, 2, 3 or 4 groups, which are identical or         different and selected from the group consisting of halogen,         C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,         or     -   R^(g), R^(h) together with the nitrogen atom, to which they are         bound may form a 5-, 6- or 7-membered, saturated or unsaturated         N-bound heterocyclic radical, which may carry as a ring member a         further heteroatom selected from O, S and N and which is         unsubstituted or may carry 1, 2, 3 or 4 groups, which are         identical or different and selected from the group consisting of         ═O, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-haloalkoxy;     -   R^(2g), R^(2h) independently of each other have the meanings         given for R^(g), R^(h);     -   R^(k) has the meanings given for R^(c);     -   R²² is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,         C₃-C₆-cycloalkyl-C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl,         phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl,         heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl,         heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl,         phenyl-N(R²³)—C₁-C₆-alkyl, heteroaryl-N(R²³)—C₁-C₆-alkyl,         heterocyclyl-N(R²³)—C₁-C₆-alkyl, phenyl-S(O)_(n)—C₁-C₆-alkyl,         heteroaryl-S(O)_(n)—C₁-C₆-alkyl,         heterocyclyl-S(O)_(n)—C₁-C₆-alkyl, where the 15 aforementioned         radicals are substituted by s residues selected from the group         consisting of nitro, halogen, cyano, rhodano, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(O)OR²³, C(O)N(R²³)₂, OR²³,         N(R²³)₂, S(O)_(n)R²⁴, S(O)₂OR²³, S(O)₂N(R²³)₂ and         R²³O—C₁-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo         groups;     -   R²³ is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl and phenyl;     -   R²⁴ is selected from the group consisting of C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₆-alkyl and phenyl;     -   R²⁵ is selected from the group consisting of C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl,         C₃-C₆-cycloalkenylene, C₃-C₆-halocycloalkyl,         C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,         C₃-C₆-cycloalkyl-C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl,         phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl,         heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl,         heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl,         phenyl-N(R²³)—C₁-C₆-alkyl, heteroaryl-N(R²³)—C₁-C₆-alkyl,         heterocyclyl-N(R²³)—C₁-C₆-alkyl, phenyl-S(O)_(n)—C₁-C₆-alkyl,         heteroaryl-S(O)_(n)—C₁-C₆-alkyl,         heterocyclyl-S(O)_(n)—C₁-C₆-alkyl, where the 15 aforementioned         radicals are substituted by s residues selected from the group         consisting of nitro, halogen, cyano, rhodano, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(O)OR²³, C(O)N(R²³)₂, OR²³,         N(R²³)₂, S(O)_(n)R²⁴, S(O)₂OR²³, S(O)₂N(R²³)₂ and         R²³O—C₁-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo         groups;     -   R²⁶ is C₁-C₆-alkyl or C₁-C₄-alkoxy-C₁-C₄-alkyl;     -   R²⁷ is selected from the group consisting of hydrogen, cyano and         C₁-C₄-haloalkylcarbonyl;     -   R²⁸, R²⁹ independently of each other are C₁-C₆-alkyl, or     -   R²⁸, R²⁹ together with the sulfur atom, to which they are bound         may form a 5- or 6-membered saturated ring, which may carry as a         ring member 1 oxygen atom;     -   k is 0, 1 or 2;     -   n is 0, 1 or 2;

The compounds of the present invention, i.e. the compounds of formula I, their N-oxides or their salts, are particularly useful for controlling unwanted vegetation. Therefore, the present invention also relates to the use of a compound of formula I, an N-oxide or a salt thereof or a composition comprising at least one compound of formula I, an N-oxide or an agriculturally suitable salt thereof for combating or controlling unwanted vegetation.

The invention also relates to a composition comprising at least one compound of the present invention, including an N-oxide or a salt thereof, and at least one auxiliary. In particular, the invention relates to an agricultural composition comprising at least one compound of the present invention, including an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.

The invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound of the present invention, including an N-oxide or a salt thereof, to act on unwanted plants, their seed and/or their habitat.

Depending on the substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group. The term “stereoisonner(s)” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).

Depending on the substitution pattern, the compounds of formula I may be present in the form of their tautomers. Hence, the invention also relates to the tautomers of the formula I and the stereoisomers, salts and N-oxides of said tautomers.

The term “N-oxide” includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides in compounds of formula I can in particular be prepared by oxidizing the ring nitrogen atom(s) of a tetrazole or a triazole with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides, or the ring nitrogen atom(s) of a heterocyclic substituent R¹, R², R³, R⁴ or R⁵.

The present invention further relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably non-radioactive isotope (e.g. hydrogen by deuterium, ¹²C by ¹³C, ¹⁴N by ¹⁵N, ¹⁶O by ¹⁸O) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom. Of course, these compounds contain more of the respective isotope than the isotope naturally occurs and thus is anyway present in the compounds of formula I.

The compounds of the present invention may be amorphous or may exist in one or more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed by customary methods, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.

Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxoniunn.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term “undesired vegetation” (“weeds”) is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location.

The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix C_(n)-C_(m) indicates in each case the possible number of carbon atoms in the group.

The term “halogen” denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term “partially or completely halogenated” means that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also “halo-radical”. For example, partially or completely halogenated alkyl is also termed haloalkyl.

The term “alkyl” as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples of C₁-C₄-alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl. Examples for C₁-C₆-alkyl are, apart from those mentioned for C₁-C₄-alkyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Examples for C₁-C₁₀-alkyl are, apart those mentioned for C₁-C₆-alkyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methyloctyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.

The term “alkylene” (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.

The term “haloalkyl” as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms (“C₁-C₈-haloalkyl”), frequently from 1 to 6 carbon atoms (“C₁-C₆-haloalkyl”), more frequently 1 to 4 carbon atoms (“C₁-C₄-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from C₁-C₄-haloalkyl, more preferably from C₁-C₂-haloalkyl, more preferably from halomethyl, in particular from C₁-C₂-fluoroalkyl. Halomethyl is methyl in which 1, 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like. Examples for C₁-C₂-fluoroalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like. Examples for C₁-C₂-haloalkyl are, apart those mentioned for C₁-C₂-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 2-chloroethyl, 2,2,-dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl, and the like. Examples for C₁-C₄-haloalkyl are, apart from those mentioned for C₁-C₂-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.

The term “cycloalkyl” as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C₃-C₁₀-cycloalkyl”), preferably 3 to 7 carbon atoms (“C₃-C₇-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C₃-C₆-cycloalkyl”). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.

The term “halocycloalkyl” as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-, 2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-, 2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.

The term “cycloalkyl-alkyl” used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkyl group. The term “C₃-C₇-cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₇-cycloalkyl group as defined above which is bound to the remainder of the molecule via a C₁-C₄-alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like.

The term “alkenyl” as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 (“C₂-C₈-alkenyl”), preferably 2 to 6 carbon atoms (“C₂-C₆-alkenyl”), in particular 2 to 4 carbon atoms (“C₂-C₄-alkenyl”), and a double bond in any position, for example C₂-C₄-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like, or C₂-C₈-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl and additionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl and the positional isomers thereof.

The term “haloalkenyl” as used herein, which may also be expressed as “alkenyl which is substituted by halogen”, and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 (“C₂-C₈-haloalkenyl”) or 2 to 6 (“C₂-C₆-haloalkenyl”) or 2 to 4 (“C₂-C₄-haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.

The term “alkynyl” as used herein denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 (“C₂-C₈-alkynyl”), frequently 2 to 6 (“C₂-C₆-alkynyl”), preferably 2 to 4 carbon atoms (“C₂-C₄-alkynyl”) and a triple bond in any position, for example C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and the like.

The term “haloalkynyl” as used herein, which is also expressed as “alkynyl which is substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms (“C₂-C₈-haloalkynyl”), frequently 2 to 6 (“C₂-C₆-haloalkynyl”), preferably 2 to 4 carbon atoms (“C₂-C₄-haloalkynyl”), and a triple bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

The term “alkoxy” as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms (“C₁-C₈-alkoxy”), frequently from 1 to 6 carbon atoms (“C₁-C₆-alkoxy”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom. C₁-C₂-alkoxy is methoxy or ethoxy. C₁-C₄-alkoxy is additionally, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C₁-C₆-alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C₁-C₈-alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.

The term “haloalkoxy” as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms (“C₁-C₈-haloalkoxy”), frequently from 1 to 6 carbon atoms (“C₁-C₆-haloalkoxy”), preferably 1 to 4 carbon atoms (“C₁-C₄-haloalkoxy”), more preferably 1 to 3 carbon atoms (“C₁-C₃-haloalkoxy”), wherein the hydrogen atoms of this group are partially or completely replaced by halogen atoms, in particular fluorine atoms. C₁-C₂-haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC₂F₅. C₁-C₄-haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy, 1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C₁-C₆-haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term “alkoxyalkyl” as used herein denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. “C₁-C₆-alkoxy-C₁-C₆-alkyl” is a C₁-C₆-alkyl group, as defined above, in which one hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above. Examples are CH₂OCH₃, CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃)₂, n-butoxymethyl, (1-methylpropoxy)-methyl, (2-methylpropoxy)methyl, CH₂—OC(CH₃)₃, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2-(1-methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1,1-dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1-methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1-methylpropoxy)-propyl, 2-(2-methylpropoxy)-propyl, 2-(1,1-dimethylethoxy)-propyl, 3-(methoxy)-propyl, 3-(ethoxy)-propyl, 3-(n-propoxy)-propyl, 3-(1-methylethoxy)-propyl, 3-(n-butoxy)-propyl, 3-(1-methylpropoxy)-propyl, 3-(2-methylpropoxy)-propyl, 3-(1,1-dimethylethoxy)-propyl, 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n-propoxy)-butyl, 2-(1-methylethoxy)-butyl, 2-(n-butoxy)-butyl, 2-(1-methylpropoxy)-butyl, 2-(2-methyl-propoxy)-butyl, 2-(1,1-dimethylethoxy)-butyl, 3-(methoxy)-butyl, 3-(ethoxy)-butyl, 3-(n-propoxy)-butyl, 3-(1-methylethoxy)-butyl, 3-(n-butoxy)-butyl, 3-(1-methylpropoxy)-butyl, 3-(2-methylpropoxy)-butyl, 3-(1,1-dimethylethoxy)-butyl, 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n-propoxy)-butyl, 4-(1-methylethoxy)-butyl, 4-(n-butoxy)-butyl, 4-(1-methylpropoxy)-butyl, 4-(2-methylpropoxy)-butyl, 4-(1,1-dimethylethoxy)-butyl and the like.

The term “haloalkoxy-alkyl” as used herein denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. Examples are fluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 1-fluoroethoxymethyl, 2-fluoroethoxymethyl, 1,1-difluoroethoxymethyl, 1,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1,1,2-trifluoroethoxymethyl, 1,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethoxymethyl, 1-fluoroethoxy-1-ethyl, 2-fluoroethoxy-1-ethyl, 1,1-difluoroethoxy-1-ethyl, 1,2-difluoroethoxy-1-ethyl, 2,2-difluoroethoxy-1-ethyl, 1,1,2-trifluoroethoxy-1-ethyl, 1,2,2-trifluoroethoxy-1-ethyl, 2,2,2-trifluoroethoxy-1-ethyl, pentafluoroethoxy-1-ethyl, 1-fluoroethoxy-2-ethyl, 2-fluoroethoxy-2-ethyl, 1,1-difluoroethoxy-2-ethyl, 1,2-difluoroethoxy-2-ethyl, 2,2-difluoroethoxy-2-ethyl, 1,1,2-trifluoroethoxy-2-ethyl, 1,2,2-trifluoroethoxy-2-ethyl, 2,2,2-trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl, and the like.

The term “alkylthio” (also alkylsulfanyl, “alkyl-S” or “alkyl-S(O)_(k)” (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms (“C₁-C₈-alkylthio”), frequently comprising 1 to 6 carbon atoms (“C₁-C₆-alkylthio”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group. C₁-C₂-alkylthio is methylthio or ethylthio. C₁-C₄-alkylthio is additionally, for example, n-propylthio, 1-methylethylthio (isopropylthio), butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1,1-dimethylethylthio (tert-butylthio). C₁-C₆-alkylthio is additionally, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio. C₁-C₈-alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.

The term “haloalkylthio” as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. C₁-C₂-haloalkylthio is, for example, SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHCl₂, SCCl₃, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC₂F₅. C₁-C₄-haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH₂—C₂F₅, SCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylthio, 1-(CH₂Cl)-2-chloroethylthio, 1-(CH₂Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C₁-C₆-haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.

The terms “alkylsulfinyl” and “alkyl-S(O)_(k)” (wherein k is 1) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For example, the term “C₁-C₂-alkylsulfinyl” refers to a C₁-C₂-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl” refers to a C₁-C₄-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C₁-C₆-alkylsulfinyl” refers to a C₁-C₆-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C₁-C₂-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C₁-C₄-alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1-methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-alkylsulfinyl is additionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.

The terms “alkylsulfonyl” and “alkyl-S(O)_(k)” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. The term “C₁-C₂-alkylsulfonyl” refers to a C₁-C₂-alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. The term “C₁-C₄-alkylsulfonyl” refers to a C₁-C₄-alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. The term “C₁-C₆-alkylsulfonyl” refers to a C₁-C₆-alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. C₁-C₂-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C₁-C₄-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1-methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl (secbutylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-alkylsulfonyl is additionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.

The term “alkylamino” as used herein denotes in each case a group R*HN—, wherein R* is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms (“C₁-C₆-alkylamino”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkylamino”). Examples of C₁-C₆-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, iso-butylamino, tert-butylamino, and the like.

The term “dialkylamino” as used herein denotes in each case a group R*R^(o)N—, wherein R* and R^(o), independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms (“di-(C₁-C₆-alkyl)-amino”), preferably 1 to 4 carbon atoms (“di-(C₁-C₄-alkyl)-amino”). Examples of a di-(C₁-C₆-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.

The suffix “-carbonyl” in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C═O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.

The term “aryl” as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.

The term “het(ero)aryl” as used herein refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrimidyl and the like.

The term “3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms as ring members selected from the groups consisting of N, O and S″ as used herein denotes monocyclic or bicyclic radicals, the monocyclic or bicyclic radicals being saturated, unsaturated or aromatic where N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO₂. An unsaturated heterocycle contains at least one C—C and/or C—N and/or N—N double bond(s). A fully unsaturated heterocycle contains as many conjugated C—C and/or C—N and/or N—N double bonds as allowed by the size(s) of the ring(s). An aromatic monocyclic heterocycle is a fully unsaturated 5- or 6-membered monocyclic heterocycle. An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring. The heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.

Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include: oxirane-2-yl, aziridine-1-yl, aziridine-2-yl, oxetan-2-yl, azetidine-1-yl, azetidine-2-yl, azetidine-3-yl, thietane-1-yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl and the like.

Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl and 1,2,4-di- or tetrahydrotriazin-3-yl.

Examples of a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring include: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include: benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.

If two radicals bound to the same nitrogen atom (for example R^(e) and R^(f) or R^(2e) and R^(2f) or R^(g) and R^(h) or R^(2g) and R^(2h)) together with the nitrogen atom, to which they are bound, form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N, this is for example pyrrolidine-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-2-yl, [1,2,3]-triazolidin-1-yl, [1,2,3]-triazolidin-2-yl, [1,2,4]-triazolidin-1-yl, [1,2,4]-triazolidin-4-yl, [1,2,3]-oxadiazolidin-2-yl, [1,2,3]-oxadiazolidin-3-yl, [1,2,5]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-4-yl, [1,3,4]-oxadiazolidin-3-yl, [1,2,3]-thiadiazolidin-2-yl, [1,2,3]-thiadiazolidin-3-yl, [1,2,5]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-4-yl, [1,3,4]-thiadiazolidin-3-yl, piperdin-1-yl, piperazine-1-yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1,1-dioxothiomorpholin-1-yl, azepan-1-yl, 1,4-diazepan-1-yl, pyrrolin-1-yl, pyrazolin-1-yl, imidazolin-1-yl, oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1-yl, 1,2-dihydropyridin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,2-dihydropyridazin, 1,6-dihydropyridazin, 1,2,3,4-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2-dihydropyrimidin, 1,6-dihydropyrimidin, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,5,6-tetrahydropyrimidin-1-yl, 1,2-dihydropyrazin-1-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,5,6-tetrahydropyrazin-1-yl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, [1,2,3]-1H-triazol-1-yl, [1,2,3]-2H-triazol-2-yl, [1,2,4]-1H-triazol-1-yl and [1,2,4]-4H-triazol-4-yl.

The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, salts, tautomers or N-oxides thereof.

The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formula I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.

Preferred compounds according to the invention are compounds of formula I or a stereoisomer, salt or N-oxide thereof, wherein the salt is an agriculturally suitable salt. Further preferred compounds according to the invention are compounds of formula I or an N-oxide or salt thereof, especially an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.

According to one embodiment of the invention the variable Q in the compounds of formula I is Q¹:

Herein, the arrow represents the binding site of the variable Q¹ conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q¹ have the following formula I.A, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ are as defined herein:

According to another embodiment of the invention the variable Q in the compounds of formula I is Q²:

Herein, the arrow represents the binding site of the variable Q² conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q² have the following formula I.B, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ are as defined herein:

According to yet further embodiment of the invention the variable Q in the compounds of formula I is Q³:

Herein, the arrow represents the binding site of the variable Q³ conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q³ have the following formula I.C, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ are as defined herein:

According to one embodiment of the invention the variable Q in the compounds of formula I is Q⁴:

Herein, the arrow represents the binding site of the variable Q⁴ conjugated to the remaining part of the compound of formula I. Compounds of formula I wherein Q is Q⁴ have the following formula I.D, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ are as defined herein:

Preferred compounds according to the invention are compounds of formula I, wherein R¹ is selected from the group consisting of cyano, halogen, nitro, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy and R^(1b)—S(O)_(k), where Z¹ is as defined in claim 1, where k is 0, 1 or 2 and where R^(1b) is selected from C₁-C₄-alkyl and C₁-C₄-haloalkyl.

Also preferred compounds according to the invention are compounds of formula I, wherein R¹ is selected from the group consisting of halogen, CN, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), where k is 0 or 2.

In a preferred embodiment, R¹ is selected from the group consisting of halogen, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsulfonyl.

In a further preferred embodiment, R¹ is selected from the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy.

In particular, R¹ is chlorine, fluorine, CF₃, CH₃, SO₂CH₃, NO₂, CH₂OCH₂CH₂OCH₃, CH(CH₂)₂ or CH₂OCH₃.

Also particular, R¹ is chlorine, CH₃, or OCH₃.

According to one group of embodiments of the present invention, R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²—;

In a preferred embodiment, R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— and R^(2c) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

In another preferred embodiment, R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— and R^(2c) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

In a preferred embodiment, R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— and R^(2d) is selected from from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

In another preferred embodiment, R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— and R^(2d) is selected from from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

In yet another preferred embodiment, R^(2c), R^(2d) together with the nitrogen atom, to which they are bound may form a 4, -5-, 6- or 7-membered, saturated or unsaturated cyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

-   -   In a preferred embodiment, R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²—         and R^(2d) is selected from from the group consisting of         hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl and benzyl.     -   In a more preferred embodiment, R² is         R^(2c)R^(2d)NC(O)NR^(2c)—Z²— and R^(2d) is selected from from         the group consisting of hydrogen, C₁-C₆-alkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,         C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, and         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl,         C₁-C₄-dialkylamino-C₁-C₄-alkyl.

Herein, particularly preferably, R^(2d) is methyl, ethyl, (C₃H₅)—CH₂—(CH₂cPr; cyclopropylmethyl) or iso-propyl. Herein, very particularly preferably, R^(2d) is methyl, ethyl, cyclopropyl or phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

Preferred compounds according to the invention are compounds of formula I, where R³ is selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy or R^(2b)—S(O)_(k), where k is 0, 1 or 2 and where R^(2b) is selected from C₁-C₄-alkyl and C₁-C₄-haloalkyl.

More preferably, R³ is selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkyl-S(O)₂ and C₁-C₄-haloalkyl-S(O)₂.

In a particular preferred embodiment, R³ is selected from the group consisting of hydrogen, halogen, C₁-C₄-haloalkyl and phenyl, where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 groups R²¹, which are identical or different.

In particular, R³ is chlorine, fluorine, CF₃, SO₂CH₃, CN, H, Br or CH₃.

More particular, R³ is hydrogen, chlorine, bromine, CF₃, or methoxyphenyl.

Preferred compounds according to the invention are compounds of formula I, where R⁴ is selected from the group consisting of hydrogen, CHF₂, CF₃, CN, NO₂, CH₃ and halogen.

More preferably, R⁴ is hydrogen, chlorine, fluorine, CN or CH₃.

According to a particular embodiment of the invention R⁴ is hydrogen, chlorine or fluorine, in particular hydrogen.

Preferred compounds according to the invention are compounds of formula I, wherein R⁵ is selected from the group consisting of CHF₂, CF₃ and halogen.

More preferably, R⁵ is halogen, in particular chlorine or fluorine, preferably fluorine.

Preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁Ca-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₄-alkoxy-C₁-C₄-alkyl.

Preferably, R⁶ may be selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, R^(c)—C(═O)—C₁-C₂-alkyl, R^(d)O—C(═O)—C₁-C₂-alkyl, R^(e)R^(f)N—C(═O)—C₁-C₂-alkyl, R^(k)—C(═O)NH—C₁-C₂-alkyl and benzyl, where

R^(c) is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R^(d) is C₁-C₄-alkyl,

R^(e) is hydrogen or C₁-C₄-alkyl,

R^(f) is hydrogen or C₁-C₄-alkyl, or

R^(e), R^(f) together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 methyl groups,

R^(k) is C₁-C₄-alkyl.

More preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁Ca-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₄-alkoxy-C₁-C₄-alkyl.

Even more preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of C₁-C₄-alkyl and C₁-C₂-alkoxy-C₁-C₂-alkyl, particularly from methyl, ethyl, n-propyl, methoxymethyl, ethoxymethyl and methoxyethyl.

Particularly preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of methyl, ethyl, n-propyl and methoxyethyl.

In this context, the variables R′, R¹¹, R²¹, Z, Z¹, Z², Z^(2a), R^(b), R^(1b), R^(2b), R^(c), R^(2c), R^(d), R^(2d), R^(e), R^(2e), R^(f), R^(2f), R^(g), R^(2g), R^(h), R^(2h), R^(k), n, k, R²², R²³, R²⁴, R²⁵, R²⁶, R²⁷, R²⁸, R²⁹, s and t, independently of each other, preferably have one of the following meanings:

R¹¹, R²¹ independently of each other are selected from halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy and C₁-C₆-haloalkyloxy; and more preferably from halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

Also more preferably R′, R¹¹, R²¹ independently of each other are selected from halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkoxy; in particular from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkoxy; and specifically from Cl, F, Br, methyl, ethyl, methoxy and trifluoromethyl.

Z, Z¹, Z² independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.

Z^(2a) is selected from a covalent bond, C₁-C₂-alkanediyl, O—C₁-C₂-alkanediyl, C₁-C₂-alkanediyl-O and C₁-C₂-alkanediyl-O—C₁-C₂-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.

R^(b), R^(1b), R^(2b) independently of each other are selected from C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl and C₁-C₂-alkoxy.

More preferably R^(b), R^(1b), R^(2b) independently of each other are selected from C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.

In particular, R^(b), R^(1b), R^(2b) independently of each other are selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.

R^(c), R^(2c), R^(k) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆ alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

More preferably R^(c), R^(2c), R^(k) independently of each other are selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂—C-alkenyl, C₂—C-haloalkenyl, C₂—C-alkynyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.

In particular, R^(c), R^(2c), R^(k) independently of each other are selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.

R^(d), R^(2d) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

More preferably R^(d), R^(2d) independently of each other are selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated; and in particular from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₃-C₆-cycloalkyl.

R^(2c), R^(2d) together with the nitrogen atom, to which they are bound may form a 4, -5-, 6- or 7-membered, saturated or unsaturated cyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R^(e), R^(f), R^(2e), R^(2f) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy, or R^(e) and R^(f) or R^(2e) and R^(2f) together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

More preferably R^(e), R^(f), R^(2e), R^(2f) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and benzyl, or R^(e) and R^(f) or R^(2e) and R^(2f) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

In particular, R^(e), R^(f), R^(2e), R^(2f) independently of each other are selected from hydrogen and C₁-C₄-alkyl, or R^(e) and R^(f) or R^(2e) and R^(2f) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 methyl groups.

R^(g), R^(2g) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl and benzyl.

More preferably R^(g), R^(2g) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, benzyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated; and in particular from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, benzyl and C₃-C₆-cycloalkyl.

R^(h), R^(2h) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl, benzyl and a radical C(═O)—R^(k), where R^(k) is H, C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenyl.

More preferably R^(h), R^(2h) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, benzyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated; and in particular from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, benzyl and C₃-C₆-cycloalkyl; or

R^(g) and R^(h) or R^(2g) and R^(2h) together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of ═O, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy;

more preferably R^(g) and R^(h) or R^(2g) and R^(2h) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

and in particular, R^(g) and R^(h) or R^(2g) and R^(2h) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 methyl groups.

n and k independently of each other are 0 or 2, and in particular 2.

R²² is selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl, phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl, heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl, where the 9 aforementioned radicals are substituted by s residues selected from the group consisting of nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C(O)OR²³, C(O)N(R²³)₂, OR²³, N(R²³)₂, S(O)_(n)R²⁴ and R²³O—C₁-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups.

More preferably R²² is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₂-alkyl, phenyl and phenyl-C₁-C₂-alkyl. In particular, R²² is hydrogen or C₁-C₄-alkyl.

R²³ is selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl. In particular, R²³ is hydrogen or C₁-C₄-alkyl.

R²⁴ is selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₃-C₆-cycloalkyl. In particular, R²⁴ is C₁-C₄-alkyl.

R²⁵ is selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl, phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl, heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl, where the 9 aforementioned radicals are substituted by s residues selected from the group consisting of nitro, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C(O)OR²³, C(O)N(R²³)₂, OR²³, N(R²³)₂, S(O)_(n)R²⁴ and R²³O—C₁-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups.

More preferably R²⁵ is selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₂-alkyl, phenyl and phenyl-C₁-C₂-alkyl. In particular, R²⁵ is C₁-C₄-alkyl.

R²⁶ is selected from the group consisting of methyl, ethyl and methoxyethyl.

R²⁷ is selected from the group consisting of hydrogen, cyano and trifluoroacetyl.

R²⁸ is ethyl and R²⁹ is ethyl, or R²⁸ and R²⁹ together are —(CH₂)₅— or —(CH₂)₂—O—(CH₂)₂—.

s is 0, 1, 2 or 3. In one particular embodiment of the invention, s is 0. In another particular embodiment of the invention, s is 1, 2 or 3.

t is 0 or 1. In one particular embodiment of the invention, t is 0. In another particular embodiment of the invention, t is 1.

Particularly preferred are compounds of formula I, wherein the variables R¹ and R³ have the following meanings:

-   R¹ is selected from the group consisting of halogen, nitro,     C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,     C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio     and C₁-C₄-alkylsulfonyl; and -   R³ is selected from the group consisting of hydrogen, halogen,     cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,     C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and     C₁-C₄-alkylsulfonyl.

Especially preferred are compounds of formula I, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ have the following meanings:

-   R¹ is selected from the group consisting of halogen, nitro,     cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkyl-S(O)₂; -   R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— with R^(2c) and R^(2d)     independently of each other selected from the group consisting of     -   hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl,         C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl,         C₁-C₄-alkamino-C₁-C₄-alkyl, C₁-C₄-dialkamino-C₁-C₄-alkyl,         C₁-C₆-cyanoalkyl and benzyl -   R³ is selected from the group consisting of hydrogen, halogen,     cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂; -   R⁴ is selected from the group consisting of hydrogen, cyano, methyl     and halogen; -   R⁵ is selected from the group consisting of halogen, CHF₂ and CF₃; -   R⁶ is selected from the group consisting of C₁-C₄-alkyl and     C₁-C₂-alkoxy-C₁-C₂-alkyl.

Also especially preferred are compounds of formula I, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ have the following meanings:

-   R¹ is selected from the group consisting of halogen, nitro,     cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl and     C₁-C₄-alkyl-S(O)₂; -   R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— with R^(2c) and R^(2d)     independently of each other selected from the group consisting of     hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,     C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in     the two aforementioned radicals are unsubstituted or partially or     completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,     C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl,     C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and     heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic     saturated, partially unsaturated or aromatic heterocycle, which     contains 1, 2, 3 or 4 heteroatoms as ring members, which are     selected from the group consisting of O, N and S, where phenyl,     benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3     or 4 groups, which are identical or different and selected from the     group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,     C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; -   R³ is selected from the group consisting of hydrogen, halogen,     cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂; -   R⁴ is selected from the group consisting of hydrogen, cyano, methyl     and halogen; -   R⁵ is selected from the group consisting of halogen, CHF₂ and CF₃; -   R⁶ is selected from the group consisting of C₁-C₄-alkyl and     C₁-C₂-alkoxy-C₁-C₂-alkyl.

Also especially preferred are compounds of formula I, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ have the following meanings:

R¹ is selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy;

R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— with R^(2c) and R^(2d) independently of each other selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;

R³ is selected from the group consisting of hydrogen, halogen, C₁-C₄-haloalkyl;

R⁴ is selected from the group consisting of hydrogen;

R⁵ is selected from the group consisting of halogen;

R⁶ is selected from the group consisting of C₁-C₄-alkyl and C₁-C₂-alkoxy-C₁-C₂-alkyl.

Specifically preferred are compounds of formula I, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ have the following meanings:

R¹ is selected from the group consisting of chlorine, methyl, methoxy;

R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— with R^(2c) and R^(2d) independently of each other selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R³ is selected from the group consisting of hydrogen, chlorine, bromine, trifluoromethyl and methoxyphenyl; R⁴ is selected from the group consisting of hydrogen; R⁵ is selected from the group consisting of fluorine; R⁶ is selected from the group consisting of methyl, ethyl, methoxyethyl and ethoxymethyl.

Specifically preferred are compounds of formula I, where the variables R¹, R², R³, R⁴, R⁵ and R⁶ have the following meanings:

-   R¹ is selected from the group consisting of chlorine, nitro, methyl,     cyclopropyl, trifluoromethyl, methoxymethyl, CH₂OCH₂CH₂OCH₃ and     methylsulfonyl; -   R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²— with R^(2c) and R^(2d)     independently of each other selected from the group consisting of     hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,     C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₁-C₄-alkoxy, C₁-C₄-alkyl -   R³ is selected from the group consisting of hydrogen, fluorine,     chlorine, bromine, cyano, nitro, methyl, trifluoromethyl and     methylsulfonyl; -   R⁴ is selected from the group consisting of hydrogen, cyano, methyl,     chlorine and fluorine; -   R⁵ is selected from the group consisting of chlorine and fluorine; -   R⁶ is selected from the group consisting of methyl, ethyl, propyl,     methoxymethyl, methoxyethyl and ethoxymethyl.

Especially preferred are compounds of formula I, where the variables R¹, R³, R⁴, R⁵ and R⁶ have the following meanings:

-   R¹ is selected from the group consisting of halogen, nitro,     cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,     C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkyl-S(O)₂; -   R³ is selected from the group consisting of hydrogen, halogen,     cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂; -   R⁴ is selected from the group consisting of hydrogen, cyano, methyl     and halogen; -   R⁵ is selected from the group consisting of halogen, CHF₂ and CF₃; -   R⁶ is selected from the group consisting of C₁-C₄-alkyl and     C₁-C₂-alkoxy-C₁-C₂-alkyl.

Especially preferred are compounds of formula I, where the variables R¹, R³, R⁴, R⁵ and R⁶ have the following meanings:

-   R¹ is selected from the group consisting of chlorine, nitro, methyl,     cyclopropyl, trifluoromethyl, methoxymethyl, CH₂OCH₂CH₂OCH₃ and     methylsulfonyl; -   R³ is selected from the group consisting of hydrogen, fluorine,     chlorine, bromine, cyano, nitro, methyl, trifluoromethyl and     methylsulfonyl; -   R⁴ is selected from the group consisting of hydrogen, cyano, methyl,     chlorine and fluorine; -   R⁵ is selected from the group consisting of chlorine and fluorine; -   R⁶ is selected from the group consisting of methyl, ethyl, propyl,     methoxymethyl, methoxyethyl and ethoxymethyl.

Specifically preferred are compounds of formula I, where the variables R¹, R³, R⁴, R⁵ and R⁶ have the following meanings:

-   -   R¹ is selected from the group consisting of chlorine, nitro,         methyl, cyclopropyl, trifluoromethyl, methoxymethyl,         CH₂OCH₂CH₂OCH₃ and methylsulfonyl;     -   R³ is selected from the group consisting of hydrogen, fluorine,         chlorine, bromine, cyano, nitro, methyl, trifluoromethyl and         methylsulfonyl;     -   R⁴ is selected from the group consisting of hydrogen, cyano,         methyl, chlorine and fluorine;     -   R⁵ is selected from the group consisting of chlorine and         fluorine;     -   R⁶ is selected from the group consisting of methyl, ethyl,         propyl, methoxymethyl, methoxyethyl and ethoxymethyl.

Examples of preferred compounds I.A, wherein Q is Q¹ and R⁴ is H, are the individual compounds compiled in Tables 1 to 20 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 1 Compounds of formula I.A (I.A-1.1-I.A-1.288) in which R² is (Me)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 2 Compounds of formula I.A (I.A-2.1-I.A-2.288) in which R² is (Me)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 3 Compounds of formula I.A (I.A-3.1-I.A-3.288) in which R² is MeEtNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 4 Compounds of formula I.A (I.A-4.1-I.A-4.288) in which R² is MeEtNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 5 Compounds of formula I.A (I.A-5.1-I.A-5.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 6 Compounds of formula I.A (I.A-6.1-I.A-6.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 7 Compounds of formula I.A (I.A-7.1-I.A-7.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 8 Compounds of formula I.A (I.A-8.1-I.A-8.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 9 Compounds of formula I.A (I.A-9.1-I.A-9.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 10 Compounds of formula I.A (I.A-10.1-I.A-10.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 11 Compounds of formula I.A (I.A-11.1-I.A-11.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 12 Compounds of formula I.A (I.A-12.1-I.A-12.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 13 Compounds of formula I.A (I.A-13.1-I.A-13.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 14 Compounds of formula I.A (I.A-14.1-I.A-14.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 15 Compounds of formula I.A (I.A-15.1-I.A-15.288) in which R² is (Et)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 16 Compounds of formula I.A (I.A-16.1-I.A-16.288) in which R² is (Et)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 17 Compounds of formula I.A (I.A-17.1-I.A-17.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 18 Compounds of formula I.A (I.A-18.1-I.A-18.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 19 Compounds of formula I.A (I.A-19.1-I.A-19.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 20 Compounds of formula I.A (I.A-20.1-I.A-20.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

TABLE A Entry R¹ R³ R⁶ A-1 Cl H CH₃ A-2 Cl H CH₂CH₃ A-3 Cl H CH₂CH₂CH₃ A-4 Cl H CH₂CH₂OCH₃ A-5 Cl F CH₃ A-6 Cl F CH₂CH₃ A-7 Cl F CH₂CH₂CH₃ A-8 Cl F CH₂CH₂OCH₃ A-9 Cl Cl CH₃ A-10 Cl Cl CH₂CH₃ A-11 Cl Cl CH₂CH₂CH₃ A-12 Cl Cl CH₂CH₂OCH₃ A-13 Cl Br CH₃ A-14 Cl Br CH₂CH₃ A-15 Cl Br CH₂CH₂CH₃ A-16 Cl Br CH₂CH₂OCH₃ A-17 Cl CN CH₃ A-18 Cl CN CH₂CH₃ A-19 Cl CN CH₂CH₂CH₃ A-20 Cl CN CH₂CH₂OCH₃ A-21 Cl CH₃ CH₃ A-22 Cl CH₃ CH₂CH₃ A-23 Cl CH₃ CH₂CH₂CH₃ A-24 Cl CH₃ CH₂CH₂OCH₃ A-25 Cl CF₃ CH₃ A-26 Cl CF₃ CH₂CH₃ A-27 Cl CF₃ CH₂CH₂CH₃ A-28 Cl CF₃ CH₂CH₂OCH₃ A-29 Cl SO₂CH₃ CH₃ A-30 Cl SO₂CH₃ CH₂CH₃ A-31 Cl SO₂CH₃ CH₂CH₂CH₃ A-32 Cl SO₂CH₃ CH₂CH₂OCH₃ A-33 Cl NO₂ CH₃ A-34 Cl NO₂ CH₂CH₃ A-35 Cl NO₂ CH₂CH₂CH₃ A-36 Cl NO₂ CH₂CH₂OCH₃ A-37 NO₂ H CH₃ A-38 NO₂ H CH₂CH₃ A-39 NO₂ H CH₂CH₂CH₃ A-40 NO₂ H CH₂CH₂OCH₃ A-41 NO₂ F CH₃ A-42 NO₂ F CH₂CH₃ A-43 NO₂ F CH₂CH₂CH₃ A-44 NO₂ F CH₂CH₂OCH₃ A-45 NO₂ Cl CH₃ A-46 NO₂ Cl CH₂CH₃ A-47 NO₂ Cl CH₂CH₂CH₃ A-48 NO₂ Cl CH₂CH₂OCH₃ A-49 NO₂ Br CH₃ A-50 NO₂ Br CH₂CH₃ A-51 NO₂ Br CH₂CH₂CH₃ A-52 NO₂ Br CH₂CH₂OCH₃ A-53 NO₂ CN CH₃ A-54 NO₂ CN CH₂CH₃ A-55 NO₂ CN CH₂CH₂CH₃ A-56 NO₂ CN CH₂CH₂OCH₃ A-57 NO₂ CH₃ CH₃ A-58 NO₂ CH₃ CH₂CH₃ A-59 NO₂ CH₃ CH₂CH₂CH₃ A-60 NO₂ CH₃ CH₂CH₂OCH₃ A-61 NO₂ CF₃ CH₃ A-62 NO₂ CF₃ CH₂CH₃ A-63 NO₂ CF₃ CH₂CH₂CH₃ A-64 NO₂ CF₃ CH₂CH₂OCH₃ A-65 NO₂ SO₂CH₃ CH₃ A-66 NO₂ SO₂CH₃ CH₂CH₃ A-67 NO₂ SO₂CH₃ CH₂CH₂CH₃ A-68 NO₂ SO₂CH₃ CH₂CH₂OCH₃ A-69 NO₂ NO₂ CH₃ A-70 NO₂ NO₂ CH₂CH₃ A-71 NO₂ NO₂ CH₂CH₂CH₃ A-72 NO₂ NO₂ CH₂CH₂OCH₃ A-73 CH₃ H CH₃ A-74 CH₃ H CH₂CH₃ A-75 CH₃ H CH₂CH₂CH₃ A-76 CH₃ H CH₂CH₂OCH₃ A-77 CH₃ F CH₃ A-78 CH₃ F CH₂CH₃ A-79 CH₃ F CH₂CH₂CH₃ A-80 CH₃ F CH₂CH₂OCH₃ A-81 CH₃ Cl CH₃ A-82 CH₃ Cl CH₂CH₃ A-83 CH₃ Cl CH₂CH₂CH₃ A-84 CH₃ Cl CH₂CH₂OCH₃ A-85 CH₃ Br CH₃ A-86 CH₃ Br CH₂CH₃ A-87 CH₃ Br CH₂CH₂CH₃ A-88 CH₃ Br CH₂CH₂OCH₃ A-89 CH₃ CN CH₃ A-90 CH₃ CN CH₂CH₃ A-91 CH₃ CN CH₂CH₂CH₃ A-92 CH₃ CN CH₂CH₂OCH₃ A-93 CH₃ CH₃ CH₃ A-94 CH₃ CH₃ CH₂CH₃ A-95 CH₃ CH₃ CH₂CH₂CH₃ A-96 CH₃ CH₃ CH₂CH₂OCH₃ A-97 CH₃ CF₃ CH₃ A-98 CH₃ CF₃ CH₂CH₃ A-99 CH₃ CF₃ CH₂CH₂CH₃ A-100 CH₃ CF₃ CH₂CH₂OCH₃ A-101 CH₃ SO₂CH₃ CH₃ A-102 CH₃ SO₂CH₃ CH₂CH₃ A-103 CH₃ SO₂CH₃ CH₂CH₂CH₃ A-104 CH₃ SO₂CH₃ CH₂CH₂OCH₃ A-105 CH₃ NO₂ CH₃ A-106 CH₃ NO₂ CH₂CH₃ A-107 CH₃ NO₂ CH₂CH₂CH₃ A-108 CH₃ NO₂ CH₂CH₂OCH₃ A-109 cyclopropyl H CH₃ A-110 cyclopropyl H CH₂CH₃ A-111 cyclopropyl H CH₂CH₂CH₃ A-112 cyclopropyl H CH₂CH₂OCH₃ A-113 cyclopropyl F CH₃ A-114 cyclopropyl F CH₂CH₃ A-115 cyclopropyl F CH₂CH₂CH₃ A-116 cyclopropyl F CH₂CH₂OCH₃ A-117 cyclopropyl Cl CH₃ A-118 cyclopropyl Cl CH₂CH₃ A-119 cyclopropyl Cl CH₂CH₂CH₃ A-120 cyclopropyl Cl CH₂CH₂OCH₃ A-121 cyclopropyl Br CH₃ A-122 cyclopropyl Br CH₂CH₃ A-123 cyclopropyl Br CH₂CH₂CH₃ A-124 cyclopropyl Br CH₂CH₂OCH₃ A-125 cyclopropyl CN CH₃ A-126 cyclopropyl CN CH₂CH₃ A-127 cyclopropyl CN CH₂CH₂CH₃ A-128 cyclopropyl CN CH₂CH₂OCH₃ A-129 cyclopropyl CH₃ CH₃ A-130 cyclopropyl CH₃ CH₂CH₃ A-131 cyclopropyl CH₃ CH₂CH₂CH₃ A-132 cyclopropyl CH₃ CH₂CH₂OCH₃ A-133 cyclopropyl CF₃ CH₃ A-134 cyclopropyl CF₃ CH₂CH₃ A-135 cyclopropyl CF₃ CH₂CH₂CH₃ A-136 cyclopropyl CF₃ CH₂CH₂OCH₃ A-137 cyclopropyl SO₂CH₃ CH₃ A-138 cyclopropyl SO₂CH₃ CH₂CH₃ A-139 cyclopropyl SO₂CH₃ CH₂CH₂CH₃ A-140 cyclopropyl SO₂CH₃ CH₂CH₂OCH₃ A-141 cyclopropyl NO₂ CH₃ A-142 cyclopropyl NO₂ CH₂CH₃ A-143 cyclopropyl NO₂ CH₂CH₂CH₃ A-144 cyclopropyl NO₂ CH₂CH₂OCH₃ A-145 CH₂OCH₃ H CH₃ A-146 CH₂OCH₃ H CH₂CH₃ A-147 CH₂OCH₃ H CH₂CH₂CH₃ A-148 CH₂OCH₃ H CH₂CH₂OCH₃ A-149 CH₂OCH₃ F CH₃ A-150 CH₂OCH₃ F CH₂CH₃ A-151 CH₂OCH₃ F CH₂CH₂CH₃ A-152 CH₂OCH₃ F CH₂CH₂OCH₃ A-153 CH₂OCH₃ Cl CH₃ A-154 CH₂OCH₃ Cl CH₂CH₃ A-155 CH₂OCH₃ Cl CH₂CH₂CH₃ A-156 CH₂OCH₃ Cl CH₂CH₂OCH₃ A-157 CH₂OCH₃ Br CH₃ A-158 CH₂OCH₃ Br CH₂CH₃ A-159 CH₂OCH₃ Br CH₂CH₂CH₃ A-160 CH₂OCH₃ Br CH₂CH₂OCH₃ A-161 CH₂OCH₃ CN CH₃ A-162 CH₂OCH₃ CN CH₂CH₃ A-163 CH₂OCH₃ CN CH₂CH₂CH₃ A-164 CH₂OCH₃ CN CH₂CH₂OCH₃ A-165 CH₂OCH₃ CH₃ CH₃ A-166 CH₂OCH₃ CH₃ CH₂CH₃ A-167 CH₂OCH₃ CH₃ CH₂CH₂CH₃ A-168 CH₂OCH₃ CH₃ CH₂CH₂OCH₃ A-169 CH₂OCH₃ CF₃ CH₃ A-170 CH₂OCH₃ CF₃ CH₂CH₃ A-171 CH₂OCH₃ CF₃ CH₂CH₂CH₃ A-172 CH₂OCH₃ CF₃ CH₂CH₂OCH₃ A-173 CH₂OCH₃ SO₂CH₃ CH₃ A-174 CH₂OCH₃ SO₂CH₃ CH₂CH₃ A-175 CH₂OCH₃ SO₂CH₃ CH₂CH₂CH₃ A-176 CH₂OCH₃ SO₂CH₃ CH₂CH₂OCH₃ A-177 CH₂OCH₃ NO₂ CH₃ A-178 CH₂OCH₃ NO₂ CH₂CH₃ A-179 CH₂OCH₃ NO₂ CH₂CH₂CH₃ A-180 CH₂OCH₃ NO₂ CH₂CH₂OCH₃ A-181 CH₂OCH₂CH₂OCH₃ H CH₃ A-182 CH₂OCH₂CH₂OCH₃ H CH₂CH₃ A-183 CH₂OCH₂CH₂OCH₃ H CH₂CH₂CH₃ A-184 CH₂OCH₂CH₂OCH₃ H CH₂CH₂OCH₃ A-185 CH₂OCH₂CH₂OCH₃ F CH₃ A-186 CH₂OCH₂CH₂OCH₃ F CH₂CH₃ A-187 CH₂OCH₂CH₂OCH₃ F CH₂CH₂CH₃ A-188 CH₂OCH₂CH₂OCH₃ F CH₂CH₂OCH₃ A-189 CH₂OCH₂CH₂OCH₃ Cl CH₃ A-190 CH₂OCH₂CH₂OCH₃ Cl CH₂CH₃ A-191 CH₂OCH₂CH₂OCH₃ Cl H₂CH₂CH₃ A-192 CH₂OCH₂CH₂OCH₃ Cl CH₂CH₂OCH₃ A-193 CH₂OCH₂CH₂OCH₃ Br CH₃ A-194 CH₂OCH₂CH₂OCH₃ Br CH₂CH₃ A-195 CH₂OCH₂CH₂OCH₃ Br H₂CH₂CH₃ A-196 CH₂OCH₂CH₂OCH₃ Br CH₂CH₂OCH₃ A-197 CH₂OCH₂CH₂OCH₃ CN CH₃ A-198 CH₂OCH₂CH₂OCH₃ CN CH₂CH₃ A-199 CH₂OCH₂CH₂OCH₃ CN H₂CH₂CH₃ A-200 CH₂OCH₂CH₂OCH₃ CN CH₂CH₂OCH₃ A-201 CH₂OCH₂CH₂OCH₃ CH₃ CH₃ A-202 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₃ A-203 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₂CH₃ A-204 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₂OCH₃ A-205 CH₂OCH₂CH₂OCH₃ CF₃ CH₃ A-206 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₃ A-207 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₂CH₃ A-208 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₂OCH₃ A-209 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₃ A-210 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₃ A-211 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₂CH₃ A-212 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₂OCH₃ A-213 CH₂OCH₂CH₂OCH₃ NO₂ CH₃ A-214 CH₂OCH₂CH₂OCH₃ NO₂ CH₂CH₃ A-215 CH₂OCH₂CH₂OCH₃ NO₂ CH₂CH₂CH₃ A-216 CH₂OCH₂CH₂OCH₃ NO₂ CH₂CH₂OCH₃ A-217 SO₂CH₃ H CH₃ A-218 SO₂CH₃ H CH₂CH₃ A-219 SO₂CH₃ H CH₂CH₂CH₃ A-220 SO₂CH₃ H CH₂CH₂OCH₃ A-221 SO₂CH₃ F CH₃ A-222 SO₂CH₃ F CH₂CH₃ A-223 SO₂CH₃ F CH₂CH₂CH₃ A-224 SO₂CH₃ F CH₂CH₂OCH₃ A-225 SO₂CH₃ Cl CH₃ A-226 SO₂CH₃ Cl CH₂CH₃ A-227 SO₂CH₃ Cl CH₂CH₂CH₃ A-228 SO₂CH₃ Cl CH₂CH₂OCH₃ A-229 SO₂CH₃ Br CH₃ A-230 SO₂CH₃ Br CH₂CH₃ A-231 SO₂CH₃ Br CH₂CH₂CH₃ A-232 SO₂CH₃ Br CH₂CH₂OCH₃ A-233 SO₂CH₃ CN CH₃ A-234 SO₂CH₃ CN CH₂CH₃ A-235 SO₂CH₃ CN CH₂CH₂CH₃ A-236 SO₂CH₃ CN CH₂CH₂OCH₃ A-237 SO₂CH₃ CH₃ CH₃ A-238 SO₂CH₃ CH₃ CH₂CH₃ A-239 SO₂CH₃ CH₃ CH₂CH₂CH₃ A-240 SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-241 SO₂CH₃ CF₃ CH₃ A-242 SO₂CH₃ CF₃ CH₂CH₃ A-243 SO₂CH₃ CF₃ CH₂CH₂CH₃ A-244 SO₂CH₃ CF₃ CH₂CH₂OCH₃ A-245 SO₂CH₃ SO₂CH₃ CH₃ A-246 SO₂CH₃ SO₂CH₃ CH₂CH₃ A-247 SO₂CH₃ SO₂CH₃ CH₂CH₂CH₃ A-248 SO₂CH₃ SO₂CH₃ CH₂CH₂OCH₃ A-249 SO₂CH₃ NO₂ CH₃ A-250 SO₂CH₃ NO₂ CH₂CH₃ A-251 SO₂CH₃ NO₂ CH₂CH₂CH₃ A-252 SO₂CH₃ NO₂ CH₂CH₂OCH₃ A-253 CF₃ H CH₃ A-254 CF₃ H CH₂CH₃ A-255 CF₃ H CH₂CH₂CH₃ A-256 CF₃ H CH₂CH₂OCH₃ A-257 CF₃ F CH₃ A-258 CF₃ F CH₂CH₃ A-259 CF₃ F CH₂CH₂CH₃ A-260 CF₃ F CH₂CH₂OCH₃ A-261 CF₃ Cl CH₃ A-262 CF₃ Cl CH₂CH₃ A-263 CF₃ Cl CH₂CH₂CH₃ A-264 CF₃ Cl CH₂CH₂OCH₃ A-265 CF₃ Br CH₃ A-266 CF₃ Br CH₂CH₃ A-267 CF₃ Br CH₂CH₂CH₃ A-268 CF₃ Br CH₂CH₂OCH₃ A-269 CF₃ CN CH₃ A-270 CF₃ CN CH₂CH₃ A-271 CF₃ CN CH₂CH₂CH₃ A-272 CF₃ CN CH₂CH₂OCH₃ A-273 CF₃ CH₃ CH₃ A-274 CF₃ CH₃ CH₂CH₃ A-275 CF₃ CH₃ CH₂CH₂CH₃ A-276 CF₃ CH₃ CH₂CH₂OCH₃ A-277 CF₃ CF₃ CH₃ A-278 CF₃ CF₃ CH₂CH₃ A-279 CF₃ CF₃ CH₂CH₂CH₃ A-280 CF₃ CF₃ CH₂CH₂OCH₃ A-281 CF₃ SO₂CH₃ CH₃ A-282 CF₃ SO₂CH₃ CH₂CH₃ A-283 CF₃ SO₂CH₃ CH₂CH₂CH₃ A-284 CF₃ SO₂CH₃ CH₂CH₂OCH₃ A-285 CF₃ NO₂ CH₃ A-286 CF₃ NO₂ CH₂CH₃ A-287 CF₃ NO₂ CH₂CH₂CH₃ A-288 CF₃ NO₂ CH₂CH₂OCH₃

Examples of preferred compounds I.B, wherein Q is Q² and R⁴ is H, are the individual compounds compiled in Tables 21 to 40 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 21 Compounds of formula I.B (I.B-1.1-I.B-1.288) in which R² is (Me)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 22 Compounds of formula I.B (I.B-2.1-I.B-2.288) in which R² is (Me)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 23 Compounds of formula I.B (I.B-3.1-I.B-3.288) in which R² is MeEtNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 24 Compounds of formula I.B (I.B-4.1-I.B-4.288) in which R² is MeEtNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 25 Compounds of formula I.B (I.B-5.1-I.B-5.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 26 Compounds of formula I.B (I.B-6.1-I.B-6.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 27 Compounds of formula I.B (I.B-7.1-I.B-7.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 28 Compounds of formula I.B (I.B-8.1-I.B-8.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 29 Compounds of formula I.B (I.B-9.1-I.B-9.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 30 Compounds of formula I.B (I.B-10.1-I.B-10.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 31 Compounds of formula I.B (I.B-11.1-I.B-11.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 32 Compounds of formula I.B (I.B-12.1-I.B-12.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 33 Compounds of formula I.B (I.B-13.1-I.B-13.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 34 Compounds of formula I.B (I.B-14.1-I.B-14.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 35 Compounds of formula I.B (I.B-15.1-I.B-15.288) in which R² is (Et)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 36 Compounds of formula I.B (I.B-16.1-I.B-16.288) in which R² is (Et)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 37 Compounds of formula I.B (I.B-17.1-I.B-17.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 38 Compounds of formula I.B (I.B-18.1-I.B-18.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 39 Compounds of formula I.B (I.B-19.1-I.B-19.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 40 Compounds of formula I.B (I.B-20.1-I.B-20.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

Examples of preferred compounds I.C, wherein Q is Q³ and R⁴ is H, are the individual compounds compiled in Tables 41 to 60 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 41 Compounds of formula I.C (I.C-1.1-I.C-1.288) in which R² is (Me)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 42 Compounds of formula I.C (I.C-2.1-I.C-2.288) in which R² is (Me)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 43 Compounds of formula I.C (I.C-3.1-I.C-3.288) in which R² is MeEtNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 44 Compounds of formula I.C (I.C-4.1-I.C-4.288) in which R² is MeEtNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 45 Compounds of formula I.C (I.C-5.1-I.C-5.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 46 Compounds of formula I.C (I.C-6.1-I.C-6.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 47 Compounds of formula I.C (I.C-7.1-I.C-7.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 48 Compounds of formula I.C (I.C-8.1-I.C-8.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 49 Compounds of formula I.C (I.C-9.1-I.C-9.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 50 Compounds of formula I.C (I.C-10.1-I.C-10.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 51 Compounds of formula I.C (I.C-11.1-I.C-11.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 52 Compounds of formula I.C (I.C-12.1-I.C-12.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 53 Compounds of formula I.C (I.C-13.1-I.C-13.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 54 Compounds of formula I.C (I.C-14.1-I.C-14.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 55 Compounds of formula I.C (I.C-15.1-I.C-15.288) in which R² is (Et)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 56 Compounds of formula I.C (I.C-16.1-I.C-16.288) in which R² is (Et)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 57 Compounds of formula I.C (I.C-17.1-I.C-17.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 58 Compounds of formula I.C (I.C-18.1-I.C-18.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 59 Compounds of formula I.C (I.C-19.1-I.C-19.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 60 Compounds of formula I.C (I.C-20.1-I.C-20.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

Examples of preferred compounds I.D, wherein Q is Q⁴ and R⁴ is H, are the individual compounds compiled in Tables 61 to 80 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 61 Compounds of formula I.D (I.A-1.1-I.D-1.288) in which R² is (Me)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 62 Compounds of formula I.D (I.A-2.1-I.D-2.288) in which R² is (Me)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 63 Compounds of formula I.D (I.A-3.1-I.D-3.288) in which R² is MeEtNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 64 Compounds of formula I.D (I.D-4.1-I.D-4.288) in which R² is MeEtNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 65 Compounds of formula I.D (I.D-5.1-I.D-5.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 66 Compounds of formula I.D (I.D-6.1-I.D-6.288) in which R² is (Me)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 67 Compounds of formula I.D (I.D-7.1-I.D-7.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 68 Compounds of formula I.D (I.D-8.1-I.D-8.288) in which R² is (Me)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 69 Compounds of formula I.D (I.D-9.1-I.D-9.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 70 Compounds of formula I.D (I.D-10.1-I.D-10.288) in which R² is (Me)(CH₃OCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 71 Compounds of formula I.D (I.D-11.1-I.D-11.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 72 Compounds of formula I.D (I.D-12.1-I.D-12.288) in which R² is (Me)(CH₃SCH₂CH₂—) NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 73 Compounds of formula I.D (I.D-13.1-I.D-13.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 74 Compounds of formula I.D (I.D-14.1-I.D-14.288) in which R² is (N-morpholino)NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 75 Compounds of formula I.D (I.D-15.1-I.D-15.288) in which R² is (Et)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 76 Compounds of formula I.D (I.D-16.1-I.D-16.288) in which R² is (Et)₂NC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 77 Compounds of formula I.D (I.D-17.1-I.D-17.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 78 Compounds of formula I.D (I.D-18.1-I.D-18.288) in which R² is (Et)iPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 79 Compounds of formula I.D (I.D-19.1-I.D-19.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 80 Compounds of formula I.D (I.D-20.1-I.D-20.288) in which R² is (Et)cPrNC(O)NH— and R⁵ is Cl and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

Further examples of preferred compounds I.A, wherein Q is Q¹ and R⁴ is H, are the individual compounds compiled in Tables 81 to 87 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 81 Compounds of formula I.A (I.A-81.1-I.A-81.288) in which R² is (iPr)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 82 Compounds of formula I.A (I.A-82.1-I.A-82.288) in which R² is (cPr)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 83 Compounds of formula I.A (I.A-83.1-I.A-83.288) in which R² is (Me)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 84 Compounds of formula I.A (I.A-84.1-I.A-84.288) in which R² is (Et)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 85 Compounds of formula I.A (I.A-85.1-I.A-85.288) in which R² is (iPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 86 Compounds of formula I.A (I.A-86.1-I.A-86.288) in which R² is (nPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 87 Compounds of formula I.A (I.A-87.1-I.A-87.288) in which R² is (Me)(4-Cl-Ph)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

Further examples of preferred compounds I.B, wherein Q is Q² and R⁴ is H, are the individual compounds compiled in Tables 88 to 94 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 88 Compounds of formula I.B (I.B-88.1-I.B-88.288) in which R² is (iPr)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 89 Compounds of formula I.B (I.B-89.1-I.B-89.288) in which R² is (cPr)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 90 Compounds of formula I.B (I.B-90.1-I.B-90.288) in which R² is (Me)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 91 Compounds of formula I.B (I.B-91.1-I.B-91.288) in which R² is (Et)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 92 Compounds of formula I.B (I.B-92.1-I.B-92.288) in which R² is (iPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 93 Compounds of formula I.B (I.B-93.1-I.B-93.288) in which R² is (nPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 94 Compounds of formula I.B (I.B-94.1-I.B-94.288) in which R² is (Me)(4-Cl-Ph)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

Further examples of preferred compounds I.C, wherein Q is Q³ and R⁴ is H, are the individual compounds compiled in Tables 95 to 101 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 95 Compounds of formula I.C (I.C-95.1-I.C-95.288) in which R² is (iPr)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 96 Compounds of formula I.C (I.C-96.1-I.C-96.288) in which R² is (cPr)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 97 Compounds of formula I.C (I.C-97.1-I.C-97.288) in which R² is (Me)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 98 Compounds of formula I.C (I.C-98.1-I.C-98.288) in which R² is (Et)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 99 Compounds of formula I.C (I.C-99.1-I.C-99.288) in which R² is (iPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 100 Compounds of formula I.C (I.C-100.1-I.C-100.288) in which R² is (nPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 101 Compounds of formula I.C (I.C-101.1-I.C-101.288) in which R² is (Me)(4-Cl-Ph)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

Further examples of preferred compounds I.D, wherein Q is Q⁴ and R⁴ is H, are the individual compounds compiled in Tables 102 to 108 below. Moreover, the meanings mentioned below for the individual variables in the Tables are, per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 102 Compounds of formula I.D (I.D-102.1-I.D-102.288) in which R² is (iPr)cPrNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 103 Compounds of formula I.D (I.D-103.1-I.D-103.288) in which R² is (cPr)₂NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 104 Compounds of formula I.D (I.D-104.1-I.D-104.288) in which R² is (Me)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 105 Compounds of formula I.D (I.D-105.1-I.D-105.288) in which R² is (Et)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 106 Compounds of formula I.D (I.D-106.1-I.D-106.288) in which R² is (iPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 107 Compounds of formula I.D (I.D-107.1-I.D-107.288) in which R² is (nPr)PhNC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A; Table 108 Compounds of formula I.D (I.D-108.1-I.D-108.288) in which R² is (Me)(4-Cl-Ph)NC(O)NH— and R⁵ is F and the combination of R¹, R³ and R⁶ for a compound corresponds in each case to one row of Table A;

The compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described in schemes 1 to 15. The substituents, variables and indices used in schemes 1 to 15 are as defined above for the compounds of formula I, if not specified otherwise.

The compounds of formula I.A can be prepared analogous to Scheme 1 below.

Likewise, the compounds of formula I.B can be prepared analogous to Scheme 2 below:

Likewise, the compounds of formula I.C can be prepared analogous to Scheme 3 below:

5-Amino-1-R-tetrazole compounds of formula III can be reacted with benzoyl derivatives of formula II to afford compounds of formula I.A. Likewise, 5-amino-1-R-1,2,4-triazole of formula IV can be reacted with benzoyl derivatives of formula II to afford compounds of formula I.B. Likewise, 4-amino-1,2,5-oxadiazole compounds of formula V can be reacted with benzoyl derivatives of formula II to afford compounds of the formula I.C. Herein, X is a leaving group, such as halogen, in particular Cl, an anhydride residue or an active ester residue. Especially in case of X being halogen the reaction is suitably carried out in the presence of a base. Suitable bases are for example carbonates, such as lithium, sodium or potassium carbonates, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6-trimethylpyridine. Suitable solvents are in particular aprotic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trimethylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof. The starting materials are generally reacted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of −20° C. to 100° C. and preferably in the range of −5° C. to 50° C.

Alternatively, compounds of formula I can also be prepared as shown in Schemes 4, 5 and 6. Reaction of 5-amino-1-R-tetrazole of formula III with a benzoic acid derivative of formula VI yields compound I.A. Likewise, reaction of 5-amino-1-R-1,2,4-triazole of formula IV with a benzoic acid derivative of formula VI yields compound I.B. Likewise, reaction of a 4-amino-1,2,5-oxadiazole compound V with a benzoic acid derivative of formula VI yields compound I.C. The reaction is preferably carried out in the presence of a suitable activating agent, which converts the acid group of compound VI into an activated ester or amide. For this purpose activating agents known in the art, such as 1,1′,carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) can be employed. The activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound V with the activating agent in the presence of compound III or IV, or in a separate step prior to the reaction with compound III or IV. It may be advantageous, especially in cases where DCC or EDC are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol or N-hydroxysuccinimide. It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine. The activated ester or amide is either in situ or subsequently reacted with the amine of formula III or IV to afford the amide of formula I. The reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. dichloromethane or dichloroethane, ethers, e.g. tetrahydrofuran or 1,4-dioxane or carboxamides, e.g. N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone. The reaction is ordinarily carried out at temperatures in the range from −20° C. to +25° C.

Furthermore, compounds of formula I.A, can be obtained by treating N-(1H-tetrazol-5-yl)benzamides of formula VII and compounds of formula I.B, can be obtained by treating N-(1H-1,2,4-triazol-5-yl)benzamides of formula VIII with, for example, alkylating agents such as alkyl halides according to Schemes 7 and 8.

The 5-amino-1-R-tetrazoles of formula III, where R⁶ is, for example, hydrogen or an alkyl, are either commercially available or are obtainable according to methods known from the literature. For example, 5-amino-1-R-tetrazole can be prepared from 5-aminotetrazole according to the method described in the Journal of the American Chemical Society, 1954, 76, 923-924 (Scheme 9).

Alternatively, 5-amino-1-R-tetrazole compounds of formula III can be prepared according to the method described in the Journal of the American Chemical Society, 1954, 76, 88-89 (Scheme 10).

As shown in Scheme 11, 5-amino-1-R-triazoles of formula IV are either commercially available or are obtainable according to methods described in the literature. For example, 5-amino-1-R-triazole can be prepared from 5-aminotriazole according to the method described in Zeitschrift für Chemie, 1990, 30, 12, 436-437.

Alternatively, 5-amino-1-R-triazole compounds of formula IV, can also be prepared analogous to the synthesis described in Chemische Berichte, 1964, 97, 2, 396-404, as shown in Scheme 12.

The compounds of formulae III, IV and V and the benzoic acid precursors of formulae II and V can be obtained by purchase or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO 9746530, WO 9831676, WO 9831681, WO 2002/018352, WO 2000/003988, US 2007/0191335, U.S. Pat. No. 6,277,847.

The 4-amino-1,2,5-oxadiazole compounds of the formula V are either commercially available or are obtainable according to methods known from the literature. For example, 3-alkyl-4-amino-1,2,5-oxadiazoles can be prepared from p-ketoesters pursuant to a procedure described in Russian Chemical Bulletin, Int. Ed., 54(4), 1032-1037 (2005), as depicted in Scheme 13.

As shown in Scheme 14, the compounds of the formula V, where R⁶ is halogen, can be prepared from commercially available 3,4-diamino-1,2,5-oxadiazole according to procedures described in the literature, e.g. by the Sandmeyer-type reaction disclosed in Heteroatom Chemistry, 15(3), 199-207 (2004).

As shown in Scheme 15, the compounds of the formula V, where R⁶ is a nucleophilic residue, can be prepared by introducing the nucleophilic residue via the substitution of a leaving group L, e.g. halogene, in the 4-position of the 1,2,5-oxadiazoles compounds of formula IX in accordance to procedures disclosed, for example in Journal of Chemical Research, Synopses (6), 190 (1985), in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (9), 2086-8 (1986) or in Russian Chemical Bulletin (Translation of Izvestiya Akademii Nauk, Seriya Khimicheskaya), 53(3), 596-614 (2004).

As a rule, the compounds of formula I including their stereoisomers, salts, tautomers and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.

The present invention also relates to a composition comprising at least one compound of formula I, an N-oxide or an agriculturally suitable salt thereof and at least one auxiliary, which is customary for formulating crop protection compounds.

The invention also relates to the use of a compound of formula I, an N-oxide or an agriculturally suitable salt thereof or a composition of the present invention for controlling unwanted vegetation.

The invention also relates to a method for controlling unwanted vegetation, which comprises allowing a herbicidally effective amount of at least one compound of formula I, an N-oxide or an agriculturally suitable salt thereof or a composition of the present invention to act on plants, their seed and/or their habitat.

The compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound I, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds of formula I, in particular the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (S. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information). Here, in general, one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) or imidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, for example, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (mutagenesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady® (glyphosate) and Liberty Link® (glufosinate) have been generated with the aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from Streptomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribosome-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase; receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pretoxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are disclosed in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the publications mentioned above. Numerous of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding for insecticidal toxins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties producing the toxin Cry1Ab), YieldGard® Plus (corn varieties which produce the toxins Cry1Ab and Cry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cotton varieties which produce the toxin Cry1Ac), Bollgard® II (cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf® (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt11 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin Cry1Ab and the PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsaturated omega 9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato).

Furthermore, it has been found that the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.

As desiccants, the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the readily controllable defoliation of useful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

The compounds of formula I, or the herbicidal compositions comprising the compounds of formula I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.

Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.

Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of formula I or Ia, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

The concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.

The compounds of formula I of the invention can for example be formulated as follows:

1. Products for Dilution with Water

A. Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.

B. Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight.

C. Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.

D. Emulsions

25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.

E. Suspensions

In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.

F. Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight.

G. Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.

H. Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active compound content of 20% by weight.

2. Products to be Applied Undiluted

I. Dusts

5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder with an active compound content of 5% by weight.

J. Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.

K. ULV Solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.

The compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the compounds of formula I or the herbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multi-layer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula I according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.

The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, cuttings and similar forms. Here, preferably, the term seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.

The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of formula I in combination with safeners. Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession.

Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diary)-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarbamates and their agriculturally useful salts and, provided that they have an acid function, their agriculturally useful derivatives, such as amides, esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, the compounds of the formula I can be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners. Suitable mixing partners are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and also phenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds of formula I alone or in combination with other herbicides or else also mixed with further crop protection agents, jointly, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Other additives such as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with the compounds of formula I according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydinn, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquatdibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlonnethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]benzamide (H-1; CAS 372137-35-4), ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (H-2; CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-6; CAS 45100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione, 2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione and 1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione;

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, fluridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7; CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the Formula 2:

in which the variables have the following meanings: Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups R^(aa); R^(A), R^(B), R^(C), R^(D) are H, halogen or C₁-C₄-alkyl; A is O or NH; q is 0 or 1. According to a preferred embodiment, the one to three groups R^(aa) are identical are different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.

Compounds of the formula 2 have in particular the following meanings:

Y is

where # denotes the bond to the skeleton of the molecule; and

R^(A), R^(B), R^(C), R^(D) are H, Cl, F or CH₃; R^(E) is halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R^(F) is C₁-C₄-alkyl; R^(G) is halogen, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R^(H) is H, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; r is 0, 1, 2 or 3; A is oxygen; q is 0 or 1.

Preferred compounds of the formula 2 have the following meanings: Y is

R^(A) is H; R^(B), R^(c) are F; R^(D) is H or F; A is oxygen; q is 0 or 1.

Particularly preferred compounds of the formula 2 are:

3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl]-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-2); 4-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-3); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-4); 4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-5); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoronnethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-6); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-8); 4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxazi-clomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyI)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO 96/26202, WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991 and from W. Krämer et al. (ed.) “Modern Crop Protection Compounds”, Vol. 1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one compound of the formula I and at least one further active compound, preferably selected from the active compounds of groups b1 to b15, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.

The invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions.

In binary compositions comprising at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In ternary compositions comprising both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative parts by weight of the components A:B are generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; and the weight ratio of the components B:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. Preferably, the weight ratio of the components A+B to the component C is in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

Examples of particularly preferred compositions according to the invention comprising in each case one individualized compound of the formula I and one mixing partner or a mixing partner combination are given in Table B below.

A further aspect of the invention relates to the compositions B-1 to B-1236 listed in Table B below, where in each case one row of Table B corresponds to a herbicidal composition comprising one of the compounds of formula I individualized in the above description (component 1) and the further active compound from groups b1) to b15) and/or safener C stated in each case in the row in question (component 2). The active compounds in the compositions described are in each case preferably present in synergistically effective amounts.

TABLE B Herbicide(s) B Safener C B-1 clodinafop-propargyl — B-2 cycloxydim — B-3 cyhalofop-butyl — B-4 fenoxaprop-P-ethyl — B-5 pinoxaden — B-6 profoxydim — B-7 tepraloxydim — B-8 tralkoxydim — B-9 esprocarb — B-10 prosulfocarb — B-11 thiobencarb — B-12 triallate — B-13 bensulfuron-methyl — B-14 bispyribac-sodium — B-15 cyclosulfamuron — B-16 flumetsulam — B-17 flupyrsulfuron-methyl-sodium — B-18 foramsulfuron — B-19 imazamox — B-20 imazapic — B-21 imazapyr — B-22 imazaquin — B-23 imazethapyr — B-24 imazosulfuron — B-25 iodosulfuron-methyl-sodium — B-26 mesosulfuron — B-27 nicosulfuron — B-28 penoxsulam — B-29 propoxycarbazone-sodium — B-30 pyrazosulfuron-ethyl — B-31 pyroxsulam — B-32 rimsulfuron — B-33 sulfosulfuron — B-34 thiencarbazone-methyl — B-35 tritosulfuron — B-36 2,4-D and its salts and esters — B-37 aminopyralid and its salts and esters — B-38 clopyralid and its salts and esters — B-39 dicamba and its salts and esters — B-40 fluroxypyr-meptyl — B-41 quinclorac — B-42 quinmerac — B-43 H-9 — B-44 diflufenzopyr — B-45 diflufenzopyr-sodium — B-46 clomazone — B-47 diflufenican — B-48 fluorochloridone — B-49 isoxaflutol — B-50 mesotrione — B-51 picolinafen — B-52 sulcotrione — B-53 tefuryltrione — B-54 tembotrione — B-55 topramezone — B-56 H-7 — B-57 atrazine — B-58 diuron — B-59 fluometuron — B-60 hexazinone — B-61 isoproturon — B-62 metribuzin — B-63 propanil — B-64 terbuthylazine — B-65 paraquat dichloride — B-66 flumioxazin — B-67 oxyfluorfen — B-68 saflufenacil — B-69 sulfentrazone — B-70 H-1 — B-71 H-2 — B-72 glyphosate — B-73 glyphosate-isopropylammonium — B-74 glyphosate-trimesium (sulfosate) — B-75 glufosinate — B-76 glufosinate-ammonium — B-77 pendimethalin — B-78 trifluralin — B-79 acetochlor — B-80 cafenstrole — B-81 dimethenamid-P — B-82 fentrazamide — B-83 flufenacet — B-84 mefenacet — B-85 metazachlor — B-86 metolachlor-S — B-87 pyroxasulfone — B-88 isoxaben — B-89 dymron — B-90 indanofan — B-91 oxaziclomefone — B-92 triaziflam — B-93 chlorotoluron — B-94 atrazine + H-1 — B-95 atrazine + glyphosate — B-96 atrazine + mesotrione — B-97 atrazine + nicosulfuron — B-98 atrazine + tembotrione — B-99 atrazine + topramezone — B-100 clomazone + glyphosate — B-101 diflufenican + clodinafop-propargyl — B-102 diflufenican + fenoxaprop-P-ethyl — B-103 diflufenican + flupyrsulfuron-methyl-sodium — B-104 diflufenican + glyphosate — B-105 diflufenican + mesosulfuron-methyl — B-106 diflufenican + pinoxaden — B-107 diflufenican + pyroxsulam — B-108 flumetsulam + glyphosate — B-109 flumioxazin + glyphosate — B-110 imazapic + glyphosate — B-111 imazethapyr + glyphosate — B-112 isoxaflutol + H-1 — B-113 isoxaflutol + glyphosate — B-114 metazachlor + H-1 — B-115 metazachlor + glyphosate — B-116 metazachlor + mesotrione — B-117 metazachlor + nicosulfuron — B-118 metazachlor + terbuthylazine — B-119 metazachlor + topramezone — B-120 metribuzin + glyphosate — B-121 pendimethalin + H-1 — B-122 pendimethalin + clodinafop-propargyl — B-123 pendimethalin + finoxaprop-P-ethyl — B-124 pendimethalin + flupyrsulfuron-methyl-sodium — B-125 pendimethalin + glyphosate — B-126 pendimethalin + mesosulfuron-methyl — B-127 pendimethalin + mesotrione — B-128 pendimethalin + nicosulfuron — B-129 pendimethalin + pinoxaden — B-130 pendimethalin + pyroxsulam — B-131 pendimethalin + tembotrione — B-132 pendimethalin + topramezone — B-133 pyroxasulfone + tembotrione — B-134 pyroxasulfone + topramezone — B-135 sulfentrazone + glyphosate — B-136 terbuthylazine + H-1 — B-137 terbuthylazine + foramsulfuron — B-138 terbuthylazine + glyphosate — B-139 terbuthylazine + mesotrione — B-140 terbuthylazine + nicosulfuron — B-141 terbuthylazine + tembotrione — B-142 terbuthylazine + topramezone — B-143 trifluralin + glyphosate — B-144 — benoxacor B-145 — cloquintocet B-146 — cyprosulfamide B-147 — dichlormid B-148 — fenchlorazole B-149 — isoxadifen B-150 — mefenpyr B-151 — H-11 B-152 — H-12 B-153 clodinafop-propargyl benoxacor B-154 cycloxydim benoxacor B-155 cyhalofop-butyl benoxacor B-156 fenoxaprop-P-ethyl benoxacor B-157 pinoxaden benoxacor B-158 profoxydim benoxacor B-159 tepraloxydim benoxacor B-160 tralkoxydim benoxacor B-161 esprocarb benoxacor B-162 prosulfocarb benoxacor B-163 thiobencarb benoxacor B-164 triallate benoxacor B-165 bensulfuron-methyl benoxacor B-166 bispyribac-sodium benoxacor B-167 cyclosulfamuron benoxacor B-168 flumetsulam benoxacor B-169 flupyrsulfuron-methyl-sodium benoxacor B-170 foramsulfuron benoxacor B-171 imazamox benoxacor B-172 imazapic benoxacor B-173 imazapyr benoxacor B-174 imazaquin benoxacor B-175 imazethapyr benoxacor B-176 imazosulfuron benoxacor B-177 iodosulfuron-methyl-sodium benoxacor B-178 mesosulfuron benoxacor B-179 nicosulfuron benoxacor B-180 penoxsulam benoxacor B-181 propoxycarbazone-sodium benoxacor B-182 pyrazosulfuron-ethyl benoxacor B-183 pyroxsulam benoxacor B-184 rimsulfuron benoxacor B-185 sulfosulfuron benoxacor B-186 thiencarbazone-methyl benoxacor B-187 tritosulfuron benoxacor B-188 2,4-D and its salts and esters benoxacor B-189 aminopyralid and its salts and esters benoxacor B-190 clopyralid and its salts and esters benoxacor B-191 dicamba and its salts and esters benoxacor B-192 fluroxypyr-meptyl benoxacor B-193 quinclorac benoxacor B-194 quinmerac benoxacor B-195 H-9 benoxacor B-196 diflufenzopyr benoxacor B-197 diflufenzopyr-sodium benoxacor B-198 clomazone benoxacor B-199 diflufenican benoxacor B-200 fluorochloridone benoxacor B-201 isoxaflutol benoxacor B-202 mesotrione benoxacor B-203 picolinafen benoxacor B-204 sulcotrione benoxacor B-205 tefuryltrione benoxacor B-206 tembotrione benoxacor B-207 topramezone benoxacor B-208 H-7 benoxacor B-209 atrazine benoxacor B-210 diuron benoxacor B-211 fluometuron benoxacor B-212 hexazinone benoxacor B-213 isoproturon benoxacor B-214 metribuzin benoxacor B-215 propanil benoxacor B-216 terbuthylazine benoxacor B-217 paraquat dichloride benoxacor B-218 flumioxazin benoxacor B-219 oxyfluorfen benoxacor B-220 saflufenacil benoxacor B-221 sulfentrazone benoxacor B-222 H-1 benoxacor B-223 H-2 benoxacor B-224 glyphosate benoxacor B-225 glyphosate-isopropylammonium benoxacor B-226 glyphosate-trimesium (sulfosate) benoxacor B-227 glufosinate benoxacor B-228 glufosinate-ammonium benoxacor B-229 pendimethalin benoxacor B-230 trifluralin benoxacor B-231 acetochlor benoxacor B-232 cafenstrole benoxacor B-233 dimethenamid-P benoxacor B-234 fentrazamide benoxacor B-235 flufenacet benoxacor B-236 mefenacet benoxacor B-237 metazachlor benoxacor B-238 metolachlor-S benoxacor B-239 pyroxasulfone benoxacor B-240 isoxaben benoxacor B-241 dymron benoxacor B-242 indanofan benoxacor B-243 oxaziclomefone benoxacor B-244 triaziflam benoxacor B-245 atrazine + H-1 benoxacor B-246 atrazine + glyphosate benoxacor B-247 atrazine + mesotrione benoxacor B-248 atrazine + nicosulfuron benoxacor B-249 atrazine + tembotrione benoxacor B-250 atrazine + topramezone benoxacor B-251 clomazone + glyphosate benoxacor B-252 diflufenican + clodinafop-propargyl benoxacor B-253 diflufenican + fenoxaprop-P-ethyl benoxacor B-254 diflufenican + flupyrsulfuron-methyl-sodium benoxacor B-255 diflufenican + glyphosate benoxacor B-256 diflufenican + mesosulfuron-methyl benoxacor B-257 diflufenican + pinoxaden benoxacor B-258 diflufenican + pyroxsulam benoxacor B-259 flumetsulam + glyphosate benoxacor B-260 flumioxazin + glyphosate benoxacor B-261 imazapic + glyphosate benoxacor B-262 imazethapyr + glyphosate benoxacor B-263 isoxaflutol + H-1 benoxacor B-264 isoxaflutol + glyphosate benoxacor B-265 metazachlor + H-1 benoxacor B-266 metazachlor + glyphosate benoxacor B-267 metazachlor + mesotrione benoxacor B-268 metazachlor + nicosulfuron benoxacor B-269 metazachlor + terbuthylazine benoxacor B-270 metazachlor + topramezone benoxacor B-271 metribuzin + glyphosate benoxacor B-272 pendimethalin + H-1 benoxacor B-273 pendimethalin + clodinafop-propargyl benoxacor B-274 pendimethalin + fenoxaprop-P-ethyl benoxacor B-275 pendimethalin + flupyrsulfuron-methyl-sodium benoxacor B-276 pendimethalin + glyphosate benoxacor B-277 pendimethalin + mesosulfuron-methyl benoxacor B-278 pendimethalin + mesotrione benoxacor B-279 pendimethalin + nicosulfuron benoxacor B-280 pendimethalin + pinoxaden benoxacor B-281 pendimethalin + pyroxsulam benoxacor B-282 pendimethalin + tembotrione benoxacor B-283 pendimethalin + topramezone benoxacor B-284 pyroxasulfone + tembotrione benoxacor B-285 pyroxasulfone + topramezone benoxacor B-286 sulfentrazone + glyphosate benoxacor B-287 terbuthylazine + H-1 benoxacor B-288 terbuthylazine + foramsulfuron benoxacor B-289 terbuthylazine + glyphosate benoxacor B-290 terbuthylazine + mesotrione benoxacor B-291 terbuthylazine + nicosulfuron benoxacor B-292 terbuthylazine + tembotrione benoxacor B-293 terbuthylazine + topramezone benoxacor B-294 trifluralin + glyphosate benoxacor B-295 clodinafop-propargyl cloquintocet B-296 cycloxydim cloquintocet B-297 cyhalofop-butyl cloquintocet B-298 fenoxaprop-P-ethyl cloquintocet B-299 pinoxaden cloquintocet B-300 profoxydim cloquintocet B-301 tepraloxydim cloquintocet B-302 tralkoxydim cloquintocet B-303 esprocarb cloquintocet B-304 prosulfocarb cloquintocet B-305 thiobencarb cloquintocet B-306 triallate cloquintocet B-307 bensulfuron-methyl cloquintocet B-308 bispyribac-sodium cloquintocet B-309 cyclosulfamuron cloquintocet B-310 flumetsulam cloquintocet B-311 flupyrsulfuron-methyl-sodium cloquintocet B-312 foramsulfuron cloquintocet B-313 imazamox cloquintocet B-314 imazapic cloquintocet B-315 imazapyr cloquintocet B-316 imazaquin cloquintocet B-317 imazethapyr cloquintocet B-318 imazosulfuron cloquintocet B-319 iodosulfuron-methyl-sodium cloquintocet B-320 mesosulfuron cloquintocet B-321 nicosulfuron cloquintocet B-322 penoxsulam cloquintocet B-323 propoxycarbazone-sodium cloquintocet B-324 pyrazosuifuron-ethyl cloquintocet B-325 pyroxsulam cloquintocet B-326 rimsulfuron cloquintocet B-327 sulfosulfuron cloquintocet B-328 thiencarbazone-methyl cloquintocet B-329 tritosulfuron cloquintocet B-330 2,4-D and its salts and esters cloquintocet B-331 aminopyralid and its salts and esters cloquintocet B-332 clopyralid and its salts and esters cloquintocet B-333 dicamba and its salts and esters cloquintocet B-334 fluroxypyr-meptyl cloquintocet B-335 quinclorac cloquintocet B-336 quinmerac cloquintocet B-337 H-9 cloquintocet B-338 diflufenzopyr cloquintocet B-339 diflufenzopyr-sodium cloquintocet B-340 clomazone cloquintocet B-341 diflufenican cloquintocet B-342 fluorochloridone cloquintocet B-343 isoxaflutol cloquintocet B-344 mesotrione cloquintocet B-345 picolinafen cloquintocet B-346 sulcotrione cloquintocet B-347 tefuryltrione cloquintocet B-348 tembotrione cloquintocet B-349 topramezone cloquintocet B-350 H-7 cloquintocet B-351 atrazine cloquintocet B-352 diuron cloquintocet B-353 fluometuron cloquintocet B-354 hexazinone cloquintocet B-355 isoproturon cloquintocet B-356 metribuzin cloquintocet B-357 propanil cloquintocet B-358 terbuthylazine cloquintocet B-359 paraquat dichloride cloquintocet B-360 flumioxazin cloquintocet B-361 oxyfluorfen cloquintocet B-362 saflufenacil cloquintocet B-363 sulfentrazone cloquintocet B-364 H-1 cloquintocet B-365 H-2 cloquintocet B-366 glyphosate cloquintocet B-367 glyphosate-isopropylammonium cloquintocet B-368 glyphosate-trimesium (sulfosate) cloquintocet B-369 glufosinate cloquintocet B-370 glufosinate-ammonium cloquintocet B-371 pendimethalin cloquintocet B-372 trifluralin cloquintocet B-373 acetochlor cloquintocet B-374 cafenstrole cloquintocet B-375 dimethenamid-P cloquintocet B-376 fentrazamide cloquintocet B-377 flufenacet cloquintocet B-378 mefenacet cloquintocet B-379 metazachlor cloquintocet B-380 metolachlor-S cloquintocet B-381 pyroxasulfone cloquintocet B-382 isoxaben cloquintocet B-383 dymron cloquintocet B-384 indanofan cloquintocet B-385 oxaziclomefone cloquintocet B-386 triaziflam cloquintocet B-387 atrazine + H-1 cloquintocet B-388 atrazine + glyphosate cloquintocet B-389 atrazine + mesotrione cloquintocet B-390 atrazine + nicosulfuron cloquintocet B-391 atrazine + tembotrione cloquintocet B-392 atrazine + topramezone cloquintocet B-393 clomazone + glyphosate cloquintocet B-394 diflufenican + clodinafop-propargyl cloquintocet B-395 diflufenican + fenoxaprop-p-ethyl cloquintocet B-396 diflufenican + flupyrsulfuron-methyl-sodium cloquintocet B-397 diflufenican + glyphosate cloquintocet B-398 diflufenican + mesosulfuron-methyl cloquintocet B-399 diflufenican + pinoxaden cloquintocet B-400 diflufenican + pyroxsulam cloquintocet B-401 flumetsulam + glyphosate cloquintocet B-402 flumioxazin + glyphosate cloquintocet B-403 imazapic + glyphosate cloquintocet B-404 imazethapyr + glyphosate cloquintocet B-405 isoxaflutol + H-1 cloquintocet B-406 isoxaflutol + glyphosate cloquintocet B-407 metazachlor + H-1 cloquintocet B-408 metazachlor + glyphosate cloquintocet B-409 metazachlor + mesotrione cloquintocet B-410 metazachlor + nicosulfuron cloquintocet B-411 metazachlor + terbuthylazine cloquintocet B-412 metazachlor + topramezone cloquintocet B-413 metribuzin + glyphosate cloquintocet B-414 pendimethalin + H-1 cloquintocet B-415 pendimethalin + clodinafop-propargyl cloquintocet B-416 pendimethalin + fenoxaprop-P-ethyl cloquintocet B-417 pendimethalin + flupyrsulfuron-methyl-sodium cloquintocet B-418 pendimethalin + glyphosate cloquintocet B-419 pendimethalin + mesosulfuron-methyl cloquintocet B-420 pendimethalin + mesotrione cloquintocet B-421 pendimethalin + nicosulfuron cloquintocet B-422 pendimethalin + pinoxaden cloquintocet B-423 pendimethalin + pyroxsulam cloquintocet B-424 pendimethalin + tembotrione cloquintocet B-425 pendimethalin + topramezone cloquintocet B-426 pyroxasulfone + tembotrione cloquintocet B-427 pyroxasulfone + topramezone cloquintocet B-428 sulfentrazone + glyphosate cloquintocet B-429 terbuthylazine + H-1 cloquintocet B-430 terbuthylazine + foramsulfuron cloquintocet B-431 terbuthylazine + glyphosate cloquintocet B-432 terbuthylazine + mesotrione cloquintocet B-433 terbuthylazine + nicosulfuron cloquintocet B-434 terbuthylazine + tembotrione cloquintocet B-435 terbuthylazine + topramezone cloquintocet B-436 trifluralin + glyphosate cloquintocet B-437 clodinafop-propargyl dichlormid B-438 cycloxydim dichlormid B-439 cyhalofop-butyl dichlormid B-440 fenoxaprop-P-ethyl dichlormid B-441 pinoxaden dichlormid B-442 profoxydim dichlormid B-443 tepraloxydim dichlormid B-444 tralkoxydim dichlormid B-445 esprocarb dichlormid B-446 prosulfocarb dichlormid B-447 thiobencarb dichlormid B-448 triallate dichlormid B-449 bensulfuron-methyl dichlormid B-450 bispyribac-sodium dichlormid B-451 cyclosulfamuron dichlormid B-452 flumetsulam dichlormid B-453 flupyrsulfuron-methyl-sodium dichlormid B-454 foramsulfuron dichlormid B-455 imazamox dichlormid B-456 imazapic dichlormid B-457 imazapyr dichlormid B-458 imazaquin dichlormid B-459 imazethapyr dichlormid B-460 imazosulfuron dichlormid B-461 iodosulfuron-methyl-sodium dichlormid B-462 mesosulfuron dichlormid B-463 nicosulfuron dichlormid B-464 penoxsulam dichlormid B-465 propoxycarbazone-sodium dichlormid B-466 pyrazosuIfuron-ethyl dichlormid B-467 pyroxsulam dichlormid B-468 rimsulfuron dichlormid B-469 sulfosulfuron dichlormid B-470 thiencarbazone-methyl dichlormid B-471 tritosulfuron dichlormid B-472 2,4-D and its salts and esters dichlormid B-473 aminopyralid and its salts and esters dichlormid B-474 clopyralid and its salts and esters dichlormid B-475 dicamba and its salts and esters dichlormid B-476 fluroxypyr-meptyl dichlormid B-477 quinclorac dichlormid B-478 quinmerac dichlormid B-479 H-9 dichlormid B-480 diflufenzopyr dichlormid B-481 diflufenzopyr-sodium dichlormid B-482 clomazone dichlormid B-483 diflufenican dichlormid B-484 fluorochloridone dichlormid B-485 isoxaflutol dichlormid B-486 mesotrione dichlormid B-487 picolinafen dichlormid B-488 sulcotrione dichlormid B-489 tefuryltrione dichlormid B-490 tembotrione dichlormid B-491 topramezone dichlormid B-492 H-7 dichlormid B-493 atrazine dichlormid B-494 diuron dichlormid B-495 fluometuron dichlormid B-496 hexazinone dichlormid B-497 isoproturon dichlormid B-498 metribuzin dichlormid B-499 propanil dichlormid B-500 terbuthylazine dichlormid B-501 paraquat dichloride dichlormid B-502 flumioxazin dichlormid B-503 oxyfluorfen dichlormid B-504 saflufenacil dichlormid B-505 sulfentrazone dichlormid B-506 H-1 dichlormid B-507 H-2 dichlormid B-508 glyphosate dichlormid B-509 glyphosate-isopropylammonium dichlormid B-510 glyphosate-trimesium (sulfosate) dichlormid B-511 glufosinate dichlormid B-512 glufosinate-ammonium dichlormid B-513 pendimethalin dichlormid B-514 trifluralin dichlormid B-515 acetochlor dichlormid B-516 cafenstrole dichlormid B-517 dimethenamid-P dichlormid B-518 fentrazamide dichlormid B-519 flufenacet dichlormid B-520 mefenacet dichlormid B-521 metazachlor dichlormid B-522 metolachlor-S dichlormid B-523 pyroxasulfone dichlormid B-524 isoxaben dichlormid B-525 dymron dichlormid B-526 indanofan dichlormid B-527 oxaziclomefone dichlormid B-528 triaziflam dichlormid B-529 atrazine + H-1 dichlormid B-530 atrazine + glyphosate dichlormid B-531 atrazine + mesotrione dichlormid B-532 atrazine + nicosulfuron dichlormid B-533 atrazine + tembotrione dichlormid B-534 atrazine + topramezone dichlormid B-535 clomazone + glyphosate dichlormid B-536 diflufenican + clodinafop-propargyl dichlormid B-537 diflufenican + fenoxaprop-p-ethyl dichlormid B-538 diflufenican + flupyrsulfuron-methyl-sodium dichlormid B-539 diflufenican + glyphosate dichlormid B-540 diflufenican + mesosulfuron-methyl dichlormid B-541 diflufenican + pinoxaden dichlormid B-542 diflufenican + pyroxsulam dichlormid B-543 flumetsulam + glyphosate dichlormid B-544 flumioxazin + glyphosate dichlormid B-545 imazapic + glyphosate dichlormid B-546 imazethapyr + glyphosate dichlormid B-547 isoxaflutol + H-1 dichlormid B-548 isoxaflutol + glyphosate dichlormid B-549 metazachlor + H-1 dichlormid B-550 metazachlor + glyphosate dichlormid B-551 metazachlor + mesotrione dichlormid B-552 metazachlor + nicosulfuron dichlormid B-553 metazachlor + terbuthylazine dichlormid B-554 metazachlor + topramezone dichlormid B-555 metribuzin + glyphosate dichlormid B-556 pendimethalin + H-1 dichlormid B-557 pendimethalin + clodinafop-propargyl dichlormid B-558 pendimethalin + fenoxaprop-P-ethyl dichlormid B-559 pendimethalin + flupyrsulfuron-methyl-sodium dichlormid B-560 pendimethalin + glyphosate dichlormid B-561 pendimethalin + mesosulfuron-methyl dichlormid B-562 pendimethalin + mesotrione dichlormid B-563 pendimethalin + nicosulfuron dichlormid B-564 pendimethalin + pinoxaden dichlormid B-565 pendimethalin + pyroxsulam dichlormid B-566 pendimethalin + tembotrione dichlormid B-567 pendimethalin + topramezone dichlormid B-568 pyroxasulfone + tembotrione dichlormid B-569 pyroxasulfone + topramezone dichlormid B-570 sulfentrazone + glyphosate dichlormid B-571 terbuthylazine + H-1 dichlormid B-572 terbuthylazine + foramsulfuron dichlormid B-573 terbuthylazine + glyphosate dichlormid B-574 terbuthylazine + mesotrione dichlormid B-575 terbuthylazine + nicosulfuron dichlormid B-576 terbuthylazine + tembotrione dichlormid B-577 terbuthylazine + topramezone dichlormid B-578 trifluralin + glyphosate dichlormid B-579 clodinafop-propargyl fenchlorazole B-580 cycloxydim fenchlorazole B-581 cyhalofop-butyl fenchlorazole B-582 fenoxaprop-P-ethyl fenchlorazole B-583 pinoxaden fenchlorazole B-584 profoxydim fenchlorazole B-585 tepraloxydim fenchlorazole B-586 tralkoxydim fenchlorazole B-587 esprocarb fenchlorazole B-588 prosulfocarb fenchlorazole B-589 thiobencarb fenchlorazole B-590 triallate fenchlorazole B-591 bensulfuron-methyl fenchlorazole B-592 bispyribac-sodium fenchlorazole B-593 cyclosulfamuron fenchlorazole B-594 flumetsulam fenchlorazole B-595 flupyrsulfuron-methyl-sodium fenchlorazole B-596 foramsulfuron fenchlorazole B-597 imazamox fenchlorazole B-598 imazapic fenchlorazole B-599 imazapyr fenchlorazole B-600 imazaquin fenchlorazole B-601 imazethapyr fenchlorazole B-602 imazosulfuron fenchlorazole B-603 iodosulfuron-methyl-sodium fenchlorazole B-604 mesosulfuron fenchlorazole B-605 nicosulfuron fenchlorazole B-606 penoxsulam fenchlorazole B-607 propoxycarbazone-sodium fenchlorazole B-608 pyrazosuifuron-ethyl fenchlorazole B-609 pyroxsulam fenchlorazole B-610 rimsulfuron fenchlorazole B-611 sulfosulfuron fenchlorazole B-612 thiencarbazone-methyl fenchlorazole B-613 tritosulfuron fenchlorazole B-614 2,4-D and its salts and esters fenchlorazole B-615 aminopyralid and its salts and esters fenchlorazole B-616 clopyralid and its salts and esters fenchlorazole B-617 dicamba and its salts and esters fenchlorazole B-618 fluroxypyr-meptyl fenchlorazole B-619 quinclorac fenchlorazole B-620 quinmerac fenchlorazole B-621 H-9 fenchlorazole B-622 diflufenzopyr fenchlorazole B-623 diflufenzopyr-sodium fenchlorazole B-624 clomazone fenchlorazole B-625 diflufenican fenchlorazole B-626 fluorochloridone fenchlorazole B-627 isoxaflutol fenchlorazole B-628 mesotrione fenchlorazole B-629 picolinafen fenchlorazole B-630 sulcotrione fenchlorazole B-631 tefuryltrione fenchlorazole B-632 tembotrione fenchlorazole B-633 topramezone fenchlorazole B-634 H-7 fenchlorazole B-635 atrazine fenchlorazole B-636 diuron fenchlorazole B-637 fluometuron fenchlorazole B-638 hexazinone fenchlorazole B-639 isoproturon fenchlorazole B-640 metribuzin fenchlorazole B-641 propanil fenchlorazole B-642 terbuthylazine fenchlorazole B-643 paraquat dichloride fenchlorazole B-644 flumioxazin fenchlorazole B-645 oxyfluorfen fenchlorazole B-646 saflufenacil fenchlorazole B-647 sulfentrazone fenchlorazole B-648 H-1 fenchlorazole B-649 H-2 fenchlorazole B-650 glyphosate fenchlorazole B-651 glyphosate-isopropylammonium fenchlorazole B-652 glyphosate-trimesium (sulfosate) fenchlorazole B-653 glufosinate fenchlorazole B-654 glufosinate-ammonium fenchlorazole B-655 pendimethalin fenchlorazole B-656 trifluralin fenchlorazole B-657 acetochlor fenchlorazole B-658 cafenstrole fenchlorazole B-659 dimethenamid-P fenchlorazole B-660 fentrazamide fenchlorazole B-661 flufenacet fenchlorazole B-662 mefenacet fenchlorazole B-663 metazachlor fenchlorazole B-664 metolachlor-S fenchlorazole B-665 pyroxasulfone fenchlorazole B-666 isoxaben fenchlorazole B-667 dymron fenchlorazole B-668 indanofan fenchlorazole B-669 oxaziclomefone fenchlorazole B-670 triaziflam fenchlorazole B-671 atrazine + H-1 fenchlorazole B-672 atrazine + glyphosate fenchlorazole B-673 atrazine + mesotrione fenchlorazole B-674 atrazine + nicosulfuron fenchlorazole B-675 atrazine + tembotrione fenchlorazole B-676 atrazine + topramezone fenchlorazole B-677 clomazone + glyphosate fenchlorazole B-678 diflufenican + clodinafop-propargyl fenchlorazole B-679 diflufenican + fenoxaprop-P-ethyl fenchlorazole B-680 diflufenican + flupyrsulfuron-methyl-sodium fenchlorazole B-681 diflufenican + glyphosate fenchlorazole B-682 diflufenican + mesosulfuron-methyl fenchlorazole B-683 diflufenican + pinoxaden fenchlorazole B-684 diflufenican + pyroxsulam fenchlorazole B-685 flumetsulam + glyphosate fenchlorazole B-686 flumioxazin + glyphosate fenchlorazole B-687 imazapic + glyphosate fenchlorazole B-688 imazethapyr + glyphosate fenchlorazole B-689 isoxaflutol + H-1 fenchlorazole B-690 isoxaflutol + glyphosate fenchlorazole B-691 metazachlor + H-1 fenchlorazole B-692 metazachlor + glyphosate fenchlorazole B-693 metazachlor + mesotrione fenchlorazole B-694 metazachlor + nicosulfuron fenchlorazole B-695 metazachlor + terbuthylazine fenchlorazole B-696 metazachlor + topramezone fenchlorazole B-697 metribuzin + glyphosate fenchlorazole B-698 pendimethalin + H-1 fenchlorazole B-699 pendimethalin + clodinafop-propargyl fenchlorazole B-700 pendimethalin + fenoxaprop-P-ethyl fenchlorazole B-701 pendimethalin + flupyrsulfuron-methyl-sodium fenchlorazole B-702 pendimethalin + glyphosate fenchlorazole B-703 pendimethalin + mesosulfuron-methyl fenchlorazole B-704 pendimethalin + mesotrione fenchlorazole B-705 pendimethalin + nicosulfuron fenchlorazole B-706 pendimethalin + pinoxaden fenchlorazole B-707 pendimethalin + pyroxsulam fenchlorazole B-708 pendimethalin + tembotrione fenchlorazole B-709 pendimethalin + topramezone fenchlorazole B-710 pyroxasulfone + tembotrione fenchlorazole B-711 pyroxasulfone + topramezone fenchlorazole B-712 sulfentrazone + glyphosate fenchlorazole B-713 terbuthylazine + H-1 fenchlorazole B-714 terbuthylazine + foramsulfuron fenchlorazole B-715 terbuthylazine + glyphosate fenchlorazole B-716 terbuthylazine + mesotrione fenchlorazole B-717 terbuthylazine + nicosulfuron fenchlorazole B-718 terbuthylazine + tembotrione fenchlorazole B-719 terbuthylazine + topramezone fenchlorazole B-720 trifluralin + glyphosate fenchlorazole B-721 clodinafop-propargyl isoxadifen B-722 cycloxydim isoxadifen B-723 cyhalofop-butyl isoxadifen B-724 fenoxaprop-P-ethyl isoxadifen B-725 pinoxaden isoxadifen B-726 profoxydim isoxadifen B-727 tepraloxydim isoxadifen B-728 tralkoxydim isoxadifen B-729 esprocarb isoxadifen B-730 prosulfocarb isoxadifen B-731 thiobencarb isoxadifen B-732 triallate isoxadifen B-733 bensulfuron-methyl isoxadifen B-734 bispyribac-sodium isoxadifen B-735 cyclosulfamuron isoxadifen B-736 flumetsulam isoxadifen B-737 flupyrsulfuron-methyl-sodium isoxadifen B-738 foramsulfuron isoxadifen B-739 imazamox isoxadifen B-740 imazapic isoxadifen B-741 imazapyr isoxadifen B-742 imazaquin isoxadifen B-743 imazethapyr isoxadifen B-744 imazosulfuron isoxadifen B-745 iodosulfuron-methyl-sodium isoxadifen B-746 mesosulfuron isoxadifen B-747 nicosulfuron isoxadifen B-748 penoxsulam isoxadifen B-749 propoxycarbazone-sodium isoxadifen B-750 pyrazosuifuron-ethyl isoxadifen B-751 pyroxsulam isoxadifen B-752 rimsulfuron isoxadifen B-753 sulfosulfuron isoxadifen B-754 thiencarbazone-methyl isoxadifen B-755 tritosulfuron isoxadifen B-756 2,4-D and its salts and esters isoxadifen B-757 aminopyralid and its salts and esters isoxadifen B-758 clopyralid and its salts and esters isoxadifen B-759 dicamba and its salts and esters isoxadifen B-760 fluroxypyr-meptyl isoxadifen B-761 quinclorac isoxadifen B-762 quinmerac isoxadifen B-763 H-9 isoxadifen B-764 diflufenzopyr isoxadifen B-765 diflufenzopyr-sodium isoxadifen B-766 clomazone isoxadifen B-767 diflufenican isoxadifen B-768 fluorochloridone isoxadifen B-769 isoxaflutol isoxadifen B-770 mesotrione isoxadifen B-771 picolinafen isoxadifen B-772 sulcotrione isoxadifen B-773 tefuryltrione isoxadifen B-774 tembotrione isoxadifen B-775 topramezone isoxadifen B-776 H-7 isoxadifen B-777 atrazine isoxadifen B-778 diuron isoxadifen B-779 fluometuron isoxadifen B-780 hexazinone isoxadifen B-781 isoproturon isoxadifen B-782 metribuzin isoxadifen B-783 propanil isoxadifen B-784 terbuthylazine isoxadifen B-785 paraquat dichloride isoxadifen B-786 flumioxazin isoxadifen B-787 oxyfluorfen isoxadifen B-788 saflufenacil isoxadifen B-789 sulfentrazone isoxadifen B-790 H-1 isoxadifen B-791 H-2 isoxadifen B-792 glyphosate isoxadifen B-793 glyphosate-isopropylammonium isoxadifen B-794 glyphosate-trimesium (sulfosate) isoxadifen B-795 glufosinate isoxadifen B-796 glufosinate-ammonium isoxadifen B-797 pendimethalin isoxadifen B-798 trifluralin isoxadifen B-799 acetochlor isoxadifen B-800 cafenstrole isoxadifen B-801 dimethenamid-P isoxadifen B-802 fentrazamide isoxadifen B-803 flufenacet isoxadifen B-804 mefenacet isoxadifen B-805 metazachlor isoxadifen B-806 metolachlor-S isoxadifen B-807 pyroxasulfone isoxadifen B-808 isoxaben isoxadifen B-809 dymron isoxadifen B-810 indanofan isoxadifen B-811 oxaziclomefone isoxadifen B-812 triaziflam isoxadifen B-813 atrazine + H-1 isoxadifen B-814 atrazine + glyphosate isoxadifen B-815 atrazine + mesotrione isoxadifen B-816 atrazine + nicosulfuron isoxadifen B-817 atrazine + tembotrione isoxadifen B-818 atrazine + topramezone isoxadifen B-819 clomazone + glyphosate isoxadifen B-820 diflufenican + clodinafop-propargyl isoxadifen B-821 diflufenican + fenoxaprop-P-ethyl isoxadifen B-822 diflufenican + flupyrsulfuron-methyl-sodium isoxadifen B-823 diflufenican + glyphosate isoxadifen B-824 diflufenican + mesosulfuron-methyl isoxadifen B-825 diflufenican + pinoxaden isoxadifen B-826 diflufenican + pyroxsulam isoxadifen B-827 flumetsulam + glyphosate isoxadifen B-828 flumioxazin + glyphosate isoxadifen B-829 imazapic + glyphosate isoxadifen B-830 imazethapyr + glyphosate isoxadifen B-831 isoxaflutol + H-1 isoxadifen B-832 isoxaflutol + glyphosate isoxadifen B-833 metazachlor + H-1 isoxadifen B-834 metazachlor + glyphosate isoxadifen B-835 metazachlor + mesotrione isoxadifen B-836 metazachlor + nicosulfuron isoxadifen B-837 metazachlor + terbuthylazine isoxadifen B-838 metazachlor + topramezone isoxadifen B-839 metribuzin + glyphosate isoxadifen B-840 pendimethalin + H-1 isoxadifen B-841 pendimethalin + clodinafop-propargyl isoxadifen B-842 pendimethalin + fenoxaprop-P-ethyl isoxadifen B-843 pendimethalin + flupyrsulfuron-methyl-sodium isoxadifen B-844 pendimethalin + glyphosate isoxadifen B-845 pendimethalin + mesosulfuron-methyl isoxadifen B-846 pendimethalin + mesotrione isoxadifen B-847 pendimethalin + nicosulfuron isoxadifen B-848 pendimethalin + pinoxaden isoxadifen B-849 pendimethalin + pyroxsulam isoxadifen B-850 pendimethalin + tembotrione isoxadifen B-851 pendimethalin + topramezone isoxadifen B-852 pyroxasulfone + tembotrione isoxadifen B-853 pyroxasulfone + topramezone isoxadifen B-854 sulfentrazone + glyphosate isoxadifen B-855 terbuthylazine + H-1 isoxadifen B-856 terbuthylazine + foramsulfuron isoxadifen B-857 terbuthylazine + glyphosate isoxadifen B-858 terbuthylazine + mesotrione isoxadifen B-859 terbuthylazine + nicosulfuron isoxadifen B-860 terbuthylazine + tembotrione isoxadifen B-861 terbuthylazine + topramezone isoxadifen B-862 trifluralin + glyphosate isoxadifen B-863 clodinafop-propargyl mefenpyr B-864 cycloxydim mefenpyr B-865 cyhalofop-butyl mefenpyr B-866 fenoxaprop-P-ethyl mefenpyr B-867 pinoxaden mefenpyr B-868 profoxydim mefenpyr B-869 tepraloxydim mefenpyr B-870 tralkoxydim mefenpyr B-871 esprocarb mefenpyr B-872 prosulfocarb mefenpyr B-873 thiobencarb mefenpyr B-874 triallate mefenpyr B-875 bensulfuron-methyl mefenpyr B-876 bispyribac-sodium mefenpyr B-877 cyclosulfamuron mefenpyr B-878 flumetsulam mefenpyr B-879 flupyrsulfuron-methyl-sodium mefenpyr B-880 foramsulfuron mefenpyr B-881 imazamox mefenpyr B-882 imazapic mefenpyr B-883 imazapyr mefenpyr B-884 imazaquin mefenpyr B-885 imazethapyr mefenpyr B-886 imazosulfuron mefenpyr B-887 iodosulfuron-methyl-sodium mefenpyr B-888 mesosulfuron mefenpyr B-889 nicosulfuron mefenpyr B-890 penoxsulam mefenpyr B-891 propoxycarbazone-sodium mefenpyr B-892 pyrazosuifuron-ethyl mefenpyr B-893 pyroxsulam mefenpyr B-894 rimsulfuron mefenpyr B-895 sulfosulfuron mefenpyr B-896 thiencarbazone-methyl mefenpyr B-897 tritosulfuron mefenpyr B-898 2,4-D and its salts and esters mefenpyr B-899 aminopyralid and its salts and esters mefenpyr B-900 clopyralid and its salts and esters mefenpyr B-901 dicamba and its salts and esters mefenpyr B-902 fluroxypyr-meptyl mefenpyr B-903 quinclorac mefenpyr B-904 quinmerac mefenpyr B-905 H-9 mefenpyr B-906 diflufenzopyr mefenpyr B-907 diflufenzopyr-sodium mefenpyr B-908 clomazone mefenpyr B-909 diflufenican mefenpyr B-910 fluorochloridone mefenpyr B-911 isoxaflutol mefenpyr B-912 mesotrione mefenpyr B-913 picolinafen mefenpyr B-914 sulcotrione mefenpyr B-915 tefuryltrione mefenpyr B-916 tembotrione mefenpyr B-917 topramezone mefenpyr B-918 H-7 mefenpyr B-919 atrazine mefenpyr B-920 diuron mefenpyr B-921 fluometuron mefenpyr B-922 hexazinone mefenpyr B-923 isoproturon mefenpyr B-924 metribuzin mefenpyr B-925 propanil mefenpyr B-926 terbuthylazine mefenpyr B-927 paraquat dichloride mefenpyr B-928 flumioxazin mefenpyr B-929 oxyfluorfen mefenpyr B-930 saflufenacil mefenpyr B-931 sulfentrazone mefenpyr B-932 H-1 mefenpyr B-933 H-2 mefenpyr B-934 glyphosate mefenpyr B-935 glyphosate-isopropylammonium mefenpyr B-936 glyphosate-trimesium (sulfosate) mefenpyr B-937 glufosinate mefenpyr B-938 glufosinate-ammonium mefenpyr B-939 pendimethalin mefenpyr B-940 trifluralin mefenpyr B-941 acetochlor mefenpyr B-942 cafenstrole mefenpyr B-943 dimethenamid-P mefenpyr B-944 fentrazamide mefenpyr B-945 flufenacet mefenpyr B-946 mefenacet mefenpyr B-947 metazachlor mefenpyr B-948 metolachlor-S mefenpyr B-949 pyroxasulfone mefenpyr B-950 isoxaben mefenpyr B-951 dymron mefenpyr B-952 indanofan mefenpyr B-953 oxaziclomefone mefenpyr B-954 triaziflam mefenpyr B-955 atrazine + H-1 mefenpyr B-956 atrazine + glyphosate mefenpyr B-957 atrazine + mesotrione mefenpyr B-958 atrazine + nicosulfuron mefenpyr B-959 atrazine + tembotrione mefenpyr B-960 atrazine + topramezone mefenpyr B-961 clomazone + glyphosate mefenpyr B-962 diflufenican + clodinafop-propargyl mefenpyr B-963 diflufenican + fenoxaprop-P-ethyl mefenpyr B-964 diflufenican + flupyrsulfuron-methyl-sodium mefenpyr B-965 diflufenican + glyphosate mefenpyr B-966 diflufenican + mesosulfuron-methyl mefenpyr B-967 diflufenican + pinoxaden mefenpyr B-968 diflufenican + pyroxsulam mefenpyr B-969 flumetsulam + glyphosate mefenpyr B-970 flumioxazin + glyphosate mefenpyr B-971 imazapic + glyphosate mefenpyr B-972 imazethapyr + glyphosate mefenpyr B-973 isoxaflutol + H-1 mefenpyr B-974 isoxaflutol + glyphosate mefenpyr B-975 metazachlor + H-1 mefenpyr B-976 metazachlor + glyphosate mefenpyr B-977 metazachlor + mesotrione mefenpyr B-978 metazachlor + nicosulfuron mefenpyr B-979 metazachlor + terbuthylazine mefenpyr B-980 metazachlor + topramezone mefenpyr B-981 metribuzin + glyphosate mefenpyr B-982 pendimethalin + H-1 mefenpyr B-983 pendimethalin + clodinafop-propargyl mefenpyr B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr B-985 pendimethalin + flupyrsulfuron-methyl-sodium mefenpyr B-986 pendimethalin + glyphosate mefenpyr B-987 pendimethalin + mesosulfuron-methyl mefenpyr B-988 pendimethalin + mesotrione mefenpyr B-989 pendimethalin + nicosulfuron mefenpyr B-990 pendimethalin + pinoxaden mefenpyr B-991 pendimethalin + pyroxsulam mefenpyr B-992 pendimethalin + tembotrione mefenpyr B-993 pendimethalin + topramezone mefenpyr B-994 pyroxasulfone + tembotrione mefenpyr B-995 pyroxasulfone + topramezone mefenpyr B-996 sulfentrazone + glyphosate mefenpyr B-997 terbuthylazine + H-1 mefenpyr B-998 terbuthylazine + foramsulfuron mefenpyr B-999 terbuthylazine + glyphosate mefenpyr B-1000 terbuthylazine + mesotrione mefenpyr B-1001 terbuthylazine + nicosulfuron mefenpyr B-1002 terbuthylazine + tembotrione mefenpyr B-1003 terbuthylazine + topramezone mefenpyr B-1004 trifluralin + glyphosate mefenpyr B-1005 clodinafop-propargyl H-12 B-1006 cycloxydim H-12 B-1007 cyhalofop-butyl H-12 B-1008 fenoxaprop-P-ethyl H-12 B-1009 pinoxaden H-12 B-1010 profoxydim H-12 B-1011 tepraloxydim H-12 B-1012 tralkoxydim H-12 B-1013 esprocarb H-12 B-1014 prosulfocarb H-12 B-1015 thiobencarb H-12 B-1016 triallate H-12 B-1017 bensulfuron-methyl H-12 B-1018 bispyribac-sodium H-12 B-1019 cyclosulfamuron H-12 B-1020 flumetsulam H-12 B-1021 flupyrsulfuron-methyl-sodium H-12 B-1022 foramsulfuron H-12 B-1023 imazamox H-12 B-1024 imazapic H-12 B-1025 imazapyr H-12 B-1026 imazaquin H-12 B-1027 imazethapyr H-12 B-1028 imazosulfuron H-12 B-1029 iodosulfuron-methyl-sodium H-12 B-1030 mesosulfuron H-12 B-1031 nicosulfuron H-12 B-1032 penoxsulam H-12 B-1033 propoxycarbazone-sodium H-12 B-1034 pyrazosuIfuron-ethyl H-12 B-1035 pyroxsulam H-12 B-1036 rimsulfuron H-12 B-1037 sulfosulfuron H-12 B-1038 thiencarbazone-methyl H-12 B-1039 tritosulfuron H-12 B-1040 2,4-D and its salts and esters H-12 B-1041 aminopyralid and its salts and esters H-12 B-1042 clopyralid and its salts and esters H-12 B-1043 dicamba and its salts and esters H-12 B-1044 fluroxypyr-meptyl H-12 B-1045 quinclorac H-12 B-1046 quinmerac H-12 B-1047 B-9 H-12 B-1048 diflufenzopyr H-12 B-1049 diflufenzopyr-sodium H-12 B-1050 clomazone H-12 B-1051 diflufenican H-12 B-1052 fluorochloridone H-12 B-1053 isoxaflutol H-12 B-1054 mesotrione H-12 B-1055 picolinafen H-12 B-1056 sulcotrione H-12 B-1057 tefuryltrione H-12 B-1058 tembotrione H-12 B-1059 topramezone H-12 B-1060 H-7 H-12 B-1061 atrazine H-12 B-1062 diuron H-12 B-1063 fluometuron H-12 B-1064 hexazinone H-12 B-1065 isoproturon H-12 B-1066 metribuzin H-12 B-1067 propanil H-12 B-1068 terbuthylazine H-12 B-1069 paraquat dichloride H-12 B-1070 flumioxazin H-12 B-1071 oxyfluorfen H-12 B-1072 saflufenacil H-12 B-1073 sulfentrazone H-12 B-1074 H-1 H-12 B-1075 H-2 H-12 B-1076 glyphosate H-12 B-1077 glyphosate-isopropylammonium H-12 B-1078 glyphosate-trimesium (sulfosate) H-12 B-1079 glufosinate H-12 B-1080 glufosinate-ammonium H-12 B-1081 pendimethalin H-12 B-1082 trifluralin H-12 B-1083 acetochlor H-12 B-1084 cafenstrole H-12 B-1085 dimethenamid-P H-12 B-1086 fentrazamide H-12 B-1087 flufenacet H-12 B-1088 mefenacet H-12 B-1089 metazachlor H-12 B-1090 metolachlor-S H-12 B-1091 pyroxasulfone H-12 B-1092 isoxaben H-12 B-1093 dymron H-12 B-1094 indanofan H-12 B-1095 oxaziclomefone H-12 B-1096 triaziflam H-12 B-1097 atrazine + H-1 H-12 B-1098 atrazine + glyphosate H-12 B-1099 atrazine + mesotrione H-12 B-1100 atrazine + nicosulfuron H-12 B-1101 atrazine + tembotrione H-12 B-1102 atrazine + topramezone H-12 B-1103 clomazone + glyphosate H-12 B-1104 diflufenican + clodinafop-propargyl H-12 B-1105 diflufenican + fenoxaprop-P-ethyl H-12 B-1106 diflufenican + flupyrsulfuron-methyl-sodium H-12 B-1107 diflufenican + glyphosate H-12 B-1108 diflufenican + menosulfuron-methyl H-12 B-1109 diflufenican + pinoxaden H-12 B-1110 diflufenican + pyroxsulam H-12 B-1111 flumetsulam + glyphosate H-12 B-1112 flumioxazin + glyphosate H-12 B-1113 imazapic + glyphosate H-12 B-1114 imazethapyr + glyphosate H-12 B-1115 isoxaflutol + H-1 H-12 B-1116 isoxaflutol + glyphosate H-12 B-1117 metazachlor + H-1 H-12 B-1118 metazachlor + glyphosate H-12 B-1119 metazachlor + mesotrione H-12 B-1120 metazachlor + nicosulfuron H-12 B-1121 metazachlor + terbuthylazine H-12 B-1122 metazachlor + topramezone H-12 B-1123 metribuzin + glyphosate H-12 B-1124 pendimethalin + H-1 H-12 B-1125 pendimethalin + clodinafop-propargyl H-12 B-1126 pendimethalin + fenoxaprop-P-ethyl H-12 B-1127 pendimethalin + flupyrsulfuron-methyl-sodium H-12 B-1128 pendimethalin + glyphosate H-12 B-1129 pendimethalin + mesosulfuron-methyl H-12 B-1130 pendimethalin + mesotrione H-12 B-1131 pendimethalin + nicosulfuron H-12 B-1132 pendimethalin + pinoxaden H-12 B-1133 pendimethalin + pyroxsulam H-12 B-1134 pendimethalin + tembotrione H-12 B-1135 pendimethalin + topramezone H-12 B-1136 pyroxasulfone + tembotrione H-12 B-1137 pyroxasulfone + topramezone H-12 B-1138 sulfentrazone + glyphosate H-12 B-1139 terbuthylazine + H-1 H-12 B-1140 terbuthylazine + foramsulfuron H-12 B-1141 terbuthylazine + glyphosate H-12 B-1142 terbuthylazine + mesotrione H-12 B-1143 terbuthylazine + nicosulfuron H-12 B-1144 terbuthylazine + tembotrione H-12 B-1145 terbuthylazine + topramezone H-12 B-1146 trifluralin + glyphosate H-12 B-1147 2-1 — B-1148 2-2 — B-1149 2-3 — B-1150 2-4 — B-1151 2-5 — B-1152 2-6 — B-1153 2-7 — B-1154 2-8 — B-1155 2-9 — B-1156 2-1 benoxacor B-1157 2-2 benoxacor B-1158 2-3 benoxacor B-1159 2-4 benoxacor B-1160 2-5 benoxacor B-1161 2-6 benoxacor B-1162 2-7 benoxacor B-1163 2-8 benoxacor B-1164 2-9 benoxacor B-1165 2-1 cloquintocet B-1166 2-2 cloquintocet B-1167 2-3 cloquintocet B-1168 2-4 cloquintocet B-1169 2-5 cloquintocet B-1170 2-6 cloquintocet B-1171 2-7 cloquintocet B-1172 2-8 cloquintocet B-1173 2-9 cloquintocet B-1174 2-1 cyprosulfamide B-1175 2-2 cyprosulfamide B-1176 2-3 cyprosulfamide B-1177 2-4 cyprosulfamide B-1178 2-5 cyprosulfamide B-1179 2-6 cyprosulfamide B-1180 2-7 cyprosulfamide B-1181 2-8 cyprosulfamide B-1182 2-9 cyprosulfamide B-1183 2-1 dichlormid B-1184 2-2 dichlormid B-1185 2-3 dichlormid B-1186 2-4 dichlormid B-1187 2-5 dichlormid B-1188 2-6 dichlormid B-1189 2-7 dichlormid B-1190 2-8 dichlormid B-1191 2-9 dichlormid B-1192 2-1 fenchlorazole B-1193 2-2 fenchlorazole B-1194 2-3 fenchlorazole B-1195 2-4 fenchlorazole B-1196 2-5 fenchlorazole B-1197 2-6 fenchlorazole B-1198 2-7 fenchlorazole B-1199 2-8 fenchlorazole B-1200 2-9 fenchlorazole B-1201 2-1 isoxadifen B-1202 2-2 isoxadifen B-1203 2-3 isoxadifen B-1204 2-4 isoxadifen B-1205 2-5 isoxadifen B-1206 2-6 isoxadifen B-1207 2-7 isoxadifen B-1208 2-8 isoxadifen B-1209 2-9 isoxadifen B-1210 2-1 mefenpyr B-1211 2-2 mefenpyr B-1212 2-3 mefenpyr B-1213 2-4 mefenpyr B-1214 2-5 mefenpyr B-1215 2-6 mefenpyr B-1216 2-7 mefenpyr B-1217 2-8 mefenpyr B-1218 2-9 mefenpyr B-1219 2-1 H-11 B-1220 2-2 H-11 B-1221 2-3 H-11 B-1222 2-4 H-11 B-1223 2-5 H-11 B-1224 2-6 H-11 B-1225 2-7 H-11 B-1226 2-8 H-11 B-1227 2-9 H-11 B-1228 2-1 H-12 B-1229 2-2 H-12 B-1230 2-3 H-12 B-1231 2-4 H-12 B-1232 2-5 H-12 B-1233 2-6 H-12 B-1234 2-7 H-12 B-1235 2-8 H-12 B-1236 2-9 H-12

The compounds of formula I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense system of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such a way that, when subsequently inoculated by unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.

The compounds of formula I can be employed for protecting plants against attack by unwanted microorganisms within a certain period of time after the treatment. The period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds of formula I, or, after treatment of the seed, for up to 9 months after sowing.

The compounds of formula I and the compositions according to the invention are also suitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by the plants.

The preparation of the compounds of formula I is illustrated by examples; however, the subject matter of the present invention is not limited to the examples given.

I. SYNTHESIS EXAMPLES

With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the table that follows, together with physical data.

The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.

HPLC-MS=high performance liquid chromatography coupled with mass spectrometry; HPLC column: 15 RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm;

mobile phase: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40′C, flow rate 1.8 ml/min.

MS: quadrupole electrospray ionization, 80 V (positive mode)

AcSK: potassium thioacetate

p-HPLC=preparative HPLC

Example 1: Preparation of 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide of the Formula I.A-3.85, Entry 7 Step 1: methyl 3-amino-4-bromo-6-fluoro-2-methyl-benzoate

Commercially available methyl 3-amino-6-fluoro-2-methyl-benzoate (CAS [848678-60-4, 30.0 g, 0.16 mol) was dissolved in anhydrous DMF (220 ml) and treated in portions with NBS (N-bromosuccinimide) at room temperature. The reaction was slightly exothermic and was kept below 29° C. via cooling. The reaction mixture was stirred overnight, concentrated in vacuo and treated with methyl-tert-butyl ether (MTBE, 450 ml) and water (400 ml) and extracted a second time with MTBE (200 ml). The combined organic phases were washed with water (3×250 ml) and brine (1×250 ml), dried over magnesium sulfate and the solvent evaporated in vacuo to yield the product (41.1 g, 96% yield). LC-MS (M+H): 263.8

Step 2: methyl 4-bromo-6-fluoro-3-isocyanato-2-methyl-benzoate

Triphosgene (bis(trichloromethyl) carbonate, 53.2 g, 0.18 mol) was dissolved in toluene (350 ml) and treated with a solution of methyl 3-amino-4-bromo-6-fluoro-2-methyl-benzoate (23.5 g, 0.09 mol) in 100 ml of toluene. Temperature was increased stepwise to reflux with evolution of gas observed starting at a temperature of approx. 85° C. Reflux was kept for 6 h and the reaction mixture stirred overnight at room temperature. Afterwards the reaction mixture was evaporated in vacuo to leave the product (15.5 g, 99%) as an orange solid which was used without further purification for the next step.

Step 3: methyl 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoate

Methyl 4-bromo-6-fluoro-3-isocyanato-2-methyl-benzoate (15.00 g, 52.07 mmol) was dissolved in THF (180 ml) and ethyl(methyl)amine (3.45 g, 59.88 mmol) was added dropwise at room temperature. The temperature increased to a maximum of 29° C. Stirring was continued overnight at RT and the solvent afterwards evaporated in vacuo. The remainder was triturated with methyl acetate several times. This gave in several portions solids yielding in total to 17.83 g (98%) of the title compound. LC-MS (M+H): 346.7

Step 4: 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoic acid

Methyl 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoate (13.95 g (40.18 mmol) was suspended in THF (250 ml) and treated with a solution of lithium hydroxide (2.89 g, 120.58 mmol) in water (50 ml) and stirred at 50° C. for 25 h. The amount of THF was reduced by concentration in vacuo and the remaining aqueous phase was washed with ethyl acetate. The pH value was adjusted to ca. pH 1-2 by addition of hydrochloric acid (1 molar). The product precipitated upon this treatment and additional cooling with ice and was filtered off. Drying in vacuo yielded 10.55 of a solid (79%) of the title compound which was used without further purification in the next step.

Step 5: 4-bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

1-Methyltetrazol-5-amine (2.38 g, 24.0 mmol) was dissolved in anhydrous THF (120 ml) and cooled to −70° C. under argon atmosphere. A solution of methyl lithium in THF (3 molar, 24.0 mmol) was added dropwise at this temperature and the reaction mixture warmed up to 0° C. At this temperature the solution prepared in the following manner was added dropwise: 4-Bromo-3-[[ethyl(methyl)carbamoyl]amino]-6-fluoro-2-methyl-benzoic acid (4.00 g, 12.0 mmol) was suspended in dichloromethane (DCM, 100 ml) and cooled to −78° C. under argon atmosphere and DAST (diethlyamino sulfur trifluoride, 2.13 g, 13.2 mmol) was added via syringe. Cooling was continued for 2.5 h and the reaction mixture afterwards allowed to warm up to RT for 15 h. The solvent was evaporated in vacuo and re-dissolved in anhydrous THF (80 ml).

After addition if this solution stirring was continued at RT for 3 h and the reaction mixture carefully quenched by addition of water (60 ml). The major amounts of THF were evaporated in vacuo and the remainder adjusted to a pH value of ca. 1 by addition of aqueous hydrochloric acid (2 molar). Extraction with ethyl acetate (3×60 ml), drying of the combined organic phases with magnesium sulfate and evaporation of the solvent yielded crude product which was purified by column chromatography to yield the title compound (1.10 g, 22%).

¹H NMR (400 MHz, MeOD), δ 7.5 (d, 1H), 4.05 (s, 3H), 3.45 (m, 2H), 3.05 (s, 3H), 2.35 (s, 3H), 1.2 (t, 3H)

Example 2: Preparation of 4-bromo-3-(diethylcarbamoylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide of the Formula I.A-15.85, Entry 5 Step 1: 6-Fluoro-2-methyl-3-nitro-benzoyl chloride

Commercially available 6-fluoro-2-methyl-3-nitro-benzoic acid (38.4 g, 193 mmol) was suspended in toluene (300 ml) and treated with thionyl chloride (21 g, 1.5 equiv.) and 2 drops of DMF and slightly warmed up while adding thionyl chloride (32.1 g, 1.4 equiv.) keeping the reaction temperature in a range of ca. 55-65° C. Gas evolved and the mixture became clear. The mixture was heated up to reflux for additional 3 hours. Evaporation in vacuo yielded the title compound in quantitative yield (42.3 g). This product was used for the next step without further purification.

Step 2: 6-Fluoro-2-methyl-N-(1-methyltetrazol-5-yl)-3-nitro-benzamide

1-Methyltetrazol-5-amine (40.2 g, 406 mmol) was dissolved in anhydrous THF (850 ml) and cooled to −75° C. under argon atmosphere. A solution of methyl lithium in THF (2.3 molar, ca. 0.4 mol) was added dropwise at this temperature and the reaction mixture warmed up to ca. 0° C. At this temperature a solution of 6-fluoro-2-methyl-3-nitro-benzoyl chloride in THF (42.3 g, 50 ml) was added keeping the temperature around 0° C. Afterwards the reaction mixture was warmed up to room temperature and stirred overnight. The reaction mixture was quenched with aqueous hydrochloric acid (200 ml, 2M) and phases separated, the organic phase dried over magnesium sulphate and the solvent evaporated to yield the crude product (42.8 g) as a solid which was used without further purification in the next step.

Step 3: 3-Amino-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

6-Fluoro-2-methyl-N-(1-methyltetrazol-5-yl)-3-nitro-benzamide (48.2 g, 172 mmol) was suspended in methanol (1 l) at RT. A solution of SnCl₂×2 H₂O (134 g, 593 mmol) in conc. hydrochloric acid (37% in water) was added in a temperature range of 45-65° C. and heated up to reflux for 2.5 h. After cooling down, the methanol was evaporated, 1 l water added and sodium hydroxide solution (50% in water) to adjust the pH to a value of about 5-6. Extraction with several portions of ethyl acetate (total of ca. 3 l), drying and evaporation led to 40.7 g (163 mmol, ca. 95% yield) of the product.

Step 4: 3-Amino-4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

3-Amino-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (20.5 g, 81.9 mmol) was suspended at RT in glacial acetic acid (260 I) and heated to 65° C. to dissolve the amine. A solution of bromine (1 equiv.) in glacial acetic acid (40 ml) was added dropwise over a period of ca. 1.5 h and the mixture stirred thereafter for additional 1.5 h. The glacial acetic acid was evaporated in vacuo and water added at ice cooling (300 ml) and stirred at this temperature for 1 h. The formed precipitate was filtered off and dried in vacuo to yield 24.5 g (91%) of the product as a lilac solid.

Step 5: 4-bromo-3-(diethylcarbamoylamino)-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide

Remark: The reaction with triphosgene leads in most cases predominantly to the formation of the imidoylchlorides as intermediates instead of the respective carboxamides, but can be converted back into a carboxamide after the formation of the urea (i.e. after addition of the respective amine to the isocyanate) by careful reaction with hydroxide solution as described in the following procedure:

A solution of 3-amino-4-bromo-6-fluoro-2-methyl-N-(1-methyltetrazol-5-yl)benzamide (10.0 g, 30.0 mmol) in n-butyl acetate was added dropwise to a solution of triphosgene (13.5 g, 45.5 mmol) in the same solvent (ca. 200 ml) and heated to reflux until the evolution of gas ceased. The solvent was evaporated in vacuo and the remainder dissolved in THF and diethyl amine added (2.34 g, ca. 1.1 equiv.) and stirred overnight. The pH value was adjusted to ca. 9 by addition of sodium hydroxide solution (2 molar in water) and stirred again overnight. Further hydroxide solution was added to reach a pH of 13 and stirring continued for 1 d. Water was added, the THF evaporate in vacuo, the aqueous phase washed with methyl tert-butyl ether and adjusted with hydrochloric acid solution to pH 5. Extraction with ethyl acetate yielded a crude product which was crystallized from ethyl acetate/methanol to yield the product (11.4 g, ca. 89%). 1H NMR (400 MHz, d6-DMSO), δ 12 (br s, 1H), 8.0 (s, 1H), 7.70 (d, 1H), 4.00 (s, 3H), 3.3 (m, 4H), 2.25 (s, 6H), 1.15 (t, 3H).

Example 3: 3-Amino-4-bromo-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide as an Example for the Preparation of Intermediates Leading to Compounds with Q², Q³ and Q⁴

3-Amino-6-fluoro-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide (3.2 g, 13 mmol), prepared from 6-fluoro-2-methyl-3-nitro-benzoic acid similar to Example 2, step 1-3 (cf. above), was dissolved in anhydrous DMF (40 ml) and treated in portions with NBS (N-bromo succinimide) at room temperature. The reaction was slightly exothermic. The reaction mixture was stirred for 4.5 h, concentrated in vacuo and treated with methyl-tert-butyl ether (MTBE, 100 ml) and water whereupon a solid was formed and separated via filtration.

The remainder was tried in vacuo and the organic phase separately dried over magnesium sulfate and the solvent evaporated in vacuo. This combined to a total von 3.67 g of the title compound.

The compounds according to Tables I to IV below were prepared in accordance with the methods described above:

TABLE I compounds of the formula I as shown above wherein Q is Q¹, R⁴ is H and R⁵ is F no. entry acc. LC-MS no. table A R¹ R³ R⁶ R² (M + H) 1 I.A-1.9 Cl Cl CH₃

376.1 2 Cl Cl CH₃

390.1 3 Cl Cl CH₃

474.1 (+Na⁺) 4 Cl Cl CH₃

424.0 5 I.A- 15.85 CH₃ Br CH₃

428.0 6 CH₃ Br CH₃

388.0 7 I.A- 3.85 CH₃ Br CH₃

416.1 8 I.A- 1.85 CH₃ Br CH₃

401.9 9 CH₃ Br CH₃

401.9 10 CH₃ Br CH₃

416.0 11 I.A- 5.85 CH₃ Br CH₃

428.0 12 CH₃ H CH₃

308.1 13 I.A- 1.81 CH₃ Cl CH₃

356.0 14 I.A- 5.81 CH₃ Cl CH₃

384.1 15 I.A- 3.84 CH₃ Cl —CH₂CH₂OCH₃

414.1 16 I.A- 3.81 CH₃ Cl CH₃

370.1 17 CH₃ Cl CH₃

356.0 18 I.A- 3.82 CH₃ Cl C₂H₅

384.1 19 CH₃ Cl C₂H₅

370.0 20 CH₃ Cl —CH₂CH₂OCH₃

400.1 21 I.A- 3.86 CH₃ Br C₂H₅

430.0 22 I.A- 3.88 CH₃ Br —CH₂CH₂OCH₃

460.0 23 CH₃ Cl —CH₂CH₂OCH₃

414.1 24 CH₃ Cl CH₃

370.0 25 CH₃ Cl —CH₂CH₂OCH₃

386.2 26 I.A- 15.81 CH₃ Cl CH₃

384.2 27 CH₃ Cl CH₃

342.1 28 CH₃ Br CH₃

430.0 29 CH₃ Br CH₃

447.9 30 CH₃ Br CH₃

428.0 31 CH₃ Br CH₃

442.1 32 I.A- 13.85 CH₃ Br CH₃

444.0 33 CH₃ Br CH₃

374.0 34 I.A- 9.85 CH₃ Br CH₃

444.0 35 CH₃ Br CH₃

460.0 36 CH₃ 4-OCH₃- phenyl CH₃

442.2 37 CH₃ Br CH₃

459.2 38 CH₃ Br CH₃

474.2 39 CH₃ Br CH₃

451.9 40 I.A- 11.85 CH₃ Br CH₃

462.1 41 CH₃ Br CH₃

416.1 42 I.A- 5.85 CH₃ Br CH₃

426.0 43 CH₃ Br CH₃

413.9 44 CH₃ Br CH₃

442.1 45 CH₃ Br CH₃

454.0 46 CH₃ Br CH₃

445.0 47 CH₃ Br CH₃

454.0 48 CH₃ Br CH₃

442.0 49 CH₃ Br CH₃

473.1 50 CH₃ Br CH₃

472.1 51 CH₃ Br CH₃

471.1 52 CH₃ Br CH₃

458.0 53 CH₃ Br CH₃

456.0 54 CH₃ Br CH₃

442.0 55 CH₃ Br CH₃

471.1 56 CH₃ Br CH₃

483.1 57 CH₃ Br CH₃

441.1 58 CH₃ Br CH₃

492.0 59 CH₃ Br CH₃

470.1 60 CH₃ Br CH₃

460.0 61 CH₃ Br CH₃

496.1 62 CH₃ Br CH₃

482.0 63 CH₃ Br CH₃

472.0 64 CH₃ Br CH₃

506.0 65 CH₃ Br CH₃

504.1 66 CH₃ Br CH₃

468.1 67 CH₃ Br CH₃

477.0 68 CH₃ Br CH₃

496.1 69 CH₃ Br CH₃

498.1 70 CH₃ Br CH₃

454.0 71 I.A- 15.25 Cl CF₃ CH₃

438.1 72 CH₃ Br CH₃

498.1 73 CH₃ Br CH₃

456.0 74 CH₃ Br CH₃

456.0 75 CH₃ Br CH₃

425.9 76 CH₃ Br CH₃

472.0 77 CH₃ Br CH₃

472.0 78 CH₃ Br CH₃

500.0 79 CH₃ Br CH₃

472.1 80 CH₃ Br CH₃

546.0 81 CH₃ Br CH₃

512.0 82 CH₃ Br CH₃

508.0 83 Cl CF₃ CH₃

500.0 84 Cl Cl CH₃

390.0 85 I.A- 15.9 Cl Cl CH₃

404.0 86 Cl Cl CH₃

428.0 87 CH₃ Br CH₃

486.0 88 CH₃ Br CH₃

445.0 89 CH₃ Br CH₃

545.9 90 CH₃ Br CH₃

554.0 91 CH₃ Br CH₃

504.0 92 CH₃ Br CH₃

443.8 93 CH₃ Br CH₃

458.0 94 CH₃ Br CH₃

580.0 95 CH₃ Br CH₃

580.0 96 CH₃ Br CH₃

531.9 97 CH₃ Br CH₃

479.9 98 CH₃ Br CH₃

559.0 99 I.A- 1.13 Cl Br CH₃

422.0 100 I.A- 3.13 Cl Br CH₃

436.0 101 CH₃ Br CH₃

442.0 102 CH₃ Br CH₃

482.1 103 I.A- 15.13 Cl Br CH₃

449.8 104 Cl Br CH₃

484.0 105 Cl Br CH₃

474.0 106 OCH₃ Br CH₃

444.1 107 CH₃ Br CH₃

478.1 108 CH₃ Br CH₃

504.0 109 CH₃ Br CH₃

494.0 110 CH₃ Br CH₃

478.0 111 CH₃ Br CH₃

498.0 112 OCH₃ Br CH₃

429.8 113 OCH₃ Br CH₃

479.8 114 OCH₃ Br CH₃

467.9 115 CH₃ Br CH₃

498.0 116 I.A-3.9 Cl Cl CH₃

390.0 117 I.A- 15.9 Cl Cl CH₃

404.0 118 Cl Cl CH₃

428.0 119 CH₃ Br CH₃

463.9 120 CH₃ Br CH₃

510.1

TABLE II compounds of the formula I as shown above wherein Q is Q², R⁴ is H and R⁵ is F no. acc. entry no. table A R¹ R³ R⁶ R² LC-MS (M + H) 1 I.B-3.85 CH₃ Br CH₃

415.0 2 CH₃ Br CH₃

462.9 3 I.B-15.85 CH₃ Br CH₃

426.9

TABLE III compounds of the formula I as shown above wherein Q is Q³, R⁴ is H and R⁵ is F no. acc. entry no. table A R¹ R³ R⁶ R² LC-MS (M + H) 1 I.C-15.85 CH₃ Br CH₃

428.1 2 I.C-1.85 CH₃ Br CH₃

401.8 3 I.C-3.85 CH₃ Br CH₃

413.9 4 CH₃ Br CH₃

462.0 5 CH₃ Br CH₃

492.0

TABLE IV compounds of the formula I as shown above wherein Q is Q⁴, R⁴ is H and R⁵ is F entry no. no. acc. table A R¹ R³ R⁶ R² LC-MS (M + H) 1 I.D-3.85 CH₃ Br CH₃

416.0 2 I.D-15.85 CH₃ Br CH₃

430.0

II. USE EXAMPLES

The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted.

This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-25° C., respectively.

The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.

At an application rate of 250 g/ha the following compounds were tested in pre-emergence tests against AMARE (Amaranthus retroflexus), CHEAL (Chenopodium album) and ECHCG (Echinocloa crus-galli) and showed a control of >85%: Entries no. 1, 5, 7, 8, 11, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 24, 26, 28, 31, 32, 33, 34.

At an application rate of 250 g/ha the following compounds were tested in post-emergence tests against

ALOMY (Alopecurus myosuroiedes) and showed a control of >85%:

Entries of Table I no. 1, 2, 5-8, 11, 13-16, 18, 21-22, 26. 28, 31, 34, 35, 39, 40 42-45, 47, 48, 50, 52-54, 58, 59, 62, 66-70, 73, 76-78, 84-86, 93, 99-100, 103-105, 115;

Entries of Table II no. 1, 2;

Entries of Table III no. 1;

ECHCG (Echinocloa crus-galli) and showed a control of >85%:

Entries Table I no. 1-3, 5-11, 13-24, 26, 28, 30-32, 34-35, 38-40, 42-45, 47-48, 50, 52-54, 58-59, 62-70, 72-74, 79, 84-87, 89-91, 93, 99, 100, 103-105, 115, 119.

Entries of Table II no. 1, 3;

AMARE (Amaranthus retroflexus) and showed a control of >85%:

Entries Table I no. 1-11, 13-28, 31-39, 42-45, 47-48, 50, 52-54, 58-59, 62-70, 73, 84-86, 91, 93, 99, 100, 103-105, 115;

Entries of Table II no. 1-3;

CHEAL (Chenopodium album) and showed a control of >85%:

Entries Table I no. 1-11, 13-29, 31-40, 42-45, 47-48, 50-54, 56-60, 62-70, 72-74, 79, 84-87, 89-91, 93, 99, 100, 103-105, 115, 119;

Entries of Table II no. 1-3;

Entries of Table III no. 1-3, 5;

Entries of Table IV no. 1; 

The invention claimed is:
 1. A compound of formula I,

an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q¹ or Q² or Q³ or Q⁴,

R¹ is selected from the group consisting of halogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl, nitro, C₁-C₄-alkoxy-C₁-C₄-alkyl, cyano-Z¹, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl-Z¹, C₂-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹, R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R¹¹, which are identical or different; R² is R^(2c)R^(2d)NC(O)NR^(2c)—Z²—; R³ is selected from the group consisting of hydrogen, halogen, hydroxy-Z², nitro, C₁-C₄-nitroalkyl, cyano, C₁-C₄-cyanoalkyl, C₁-C₆-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl-Z², C₃-C₁₀-cycloalkoxy-Z², where the C₃-C₁₀-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₈-alkoxy-Z², C₁-C₈-haloalkoxy-Z², C₃-C₁₀-cycloalkyl-C₁-C₂-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z², C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z², C₂-C₈-alkenyloxy-Z², C₂-C₈-alkynyloxy-Z², C₂-C₈-haloalkenyloxy-Z², C₃-C₈-haloalkynyloxy-Z², C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z², (tri-C₁-C₄-alkyl)silyl-Z², R^(2b)-S(O)_(k)-Z², R^(2c)-C(═O)—Z², R^(2d)O—C(═O)—Z², R^(2d)O—N═CH—Z², R^(2e)R^(2f)N—C(═O)—Z², R^(2g)R^(2h)N—Z², phenyl-Z^(2a), heterocyclyl-Z^(2a), where heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenyl-Z^(2a) and heterocy-clyl-Z^(2a) are unsubstituted or substituted by 1, 2, 3 or 4 groups R²¹, which are identical or different, rhodano, C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkenyl, C₃-C₆-cycloalkenyl-C₁-C₆-alkyl, C₃-C₆-halocycloalkenyl-C₁-C₆-alkyl, OC(O)R²², OC(O)OR²⁵, OC(O)N(R²²)₂, OSO₂R²⁵, SO₂OR²², SO₂N(R²²)₂, SO₂N(R²²)C(O)R²², SO₂N(R²²)C(O)OR²⁵, SO₂N(R²²)C(O)N(R²²)₂, N(R²²)C(O)OR²⁵, N(R²²)C(O)N(R²²)₂, N(R²²)S(O)₂OR²², N(R²²)S(O)₂N(R²²)₂, C(O)N(R²²)OR²², C(O)N(R²²)N(R²²)₂, C(O)N(R²²)C(O)R²², C(O)N(R²²)C(O)OR²⁵, C(O)N(R²²)C(O)N(R²²)₂, C(O)N(R²²)SO₂R²⁵, C(O)N(R²²)SO₂OR²², C(O)N(R²²)SO₂N(R²²)₂, P(O)(OH)₂, P(O)(O—C₁-C₄-alkyl)₂, C₁-C₆-alkyl-OC(O)R²², C₁-C₆-alkyl-OC(O)OR²⁵, C₁-C₆-alkyl-OC(O)N(R²²)₂, C₁-C₆-alkyl-OSO₂R²⁵, C₁-C₆-alkyl-SO₂OR²², C₁-C₆-alkyl-SO₂N(R²²)₂, C₁-C₆-alkyl-SO₂N(R²²)C(O)R²², C₁-C₆-alkyl-SO₂N(R²²)C(O)OR²⁵, C₁-C₆-alkyl-SO₂N(R²²)C(O)N(R²²)₂, C₁-C₆-alkyl-N(R²²)C(O)OR²⁵, C₁-C₆-alkyl-N(R²²)C(O)N(R²²)₂, C₁-C₆-alkyl-N(R²²)S(O)₂OR²², C₁-C₆-alkyl-N(R²²)S(O)₂N(R²²)₂, C₁-C₆-alkyl-C(O)N(R²²)OR²², C₁-C₆-alkyl-C(O)N(R²²)N(R²²)₂, C₁-C₆-alkyl-C(O)N(R²²)C(O)R²², C₁-C₆-alkyl-C(O)N(R²²)C(O)OR²⁵, C₁-C₆-alkyl-C(O)N(R²²)C(O)N(R²²)₂, C₁-C₆-alkyl-C(O)N(R²²)SO₂R²⁵, C₁-C₆-alkyl-C(O)N(R²²)SO₂OR²², C₁-C₆-alkyl-C(O)N(R²²)SO₂N(R²²)₂, C₁-C₆-alkyl-P(O)(OH)₂ and C₁-C₆-alkyl-P(O)(O—C₁-C₄-alkyl)₂; R⁴ is selected from the group consisting of hydrogen, halogen, C₁-C₈-alkyl, cyano-Z¹, nitro, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino, C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k), C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹, R^(1b)-S(O)_(k)-Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R¹¹, which are identical or different; R⁵ is selected from the group consisting of halogen, cyano-Z¹, nitro, C₁-C₈-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino, C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k), C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹, R^(1b)-S(O)_(k)-Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R¹¹, which are identical or different; R⁶ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, R^(b)-S(O)_(n)—C₁-C₃-alkyl, R^(c)—C(═O)—C₁-C₃-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl, R^(e)R^(f)N—C(═O)—C₁-C₃-alkyl, R^(g)R^(h)N—C₁-C₃-alkyl, phenyl-Z and heterocyclyl-Z, where heterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R′, which are identical or different; R′, R¹¹, R²¹ independently of each other are selected from the group consisting of halogen, NO₂, CN, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₃-C₇-cycloalkoxy and C₁-C₆-haloalkyloxy, or two radicals R′, R¹¹ or R²¹ bound to the same carbon atom together may form a group ═O; Z, Z¹, Z² independently of each other are selected from the group consisting of a covalent bond and C₁-C₄-alkanediyl; Z^(2a) is selected from the group consisting of a covalent bond, C₁-C₄-alkanediyl, O—C₁-C₄-alkanediyl, C₁-C₄-alkanediyl-O and C₁-C₄-alkanediyl-O—C₁-C₄-alkanediyl; R^(b), R^(1b), R^(2b) independently of each other are selected from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(c), R^(2c) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(d), R^(2d) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(2c), R^(2d) together with the nitrogen atom, to which they are bound may form a 4, -5-, 6- or 7-membered, saturated or unsaturated cyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(e), R^(f) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenylene, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or R^(e), R^(f) together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(2e), R^(2f) independently of each other have the meanings given for R^(e), R^(f); R^(g) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenylene, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(h) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, a radical C(═O)—R^(k), phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or R^(g), R^(h) together with the nitrogen atom, to which they are bound may form a 5-, 6- or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of ═O, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(2g), R^(2h) independently of each other have the meanings given for R^(g), R^(h); R^(k) has the meanings given for R^(c); R²² is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenyl, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl, phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl, heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl, phenyl-N(R²³)—C₁-C₆-alkyl, heteroaryl-N(R²³)—C₁-C₆-alkyl, heterocyclyl-N(R²³)—C₁-C₆-alkyl, phenyl-S(O)_(n)—C₁-C₆-alkyl, heteroaryl-S(O)_(n)—C₁-C₆-alkyl, heterocyclyl-S(O)_(n)—C₁-C₆-alkyl, where the 15 aforementioned phenyl, phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl, heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl, phenyl-N(R²³)—C₁-C₆-alkyl, heteroaryl-N(R²³)—C₁-C₆-alkyl, heterocyclyl-N(R²³)—C₁-C₆-alkyl, phenyl-S(O)_(n)—C₁-C₆-alkyl, heteroaryl-S(O)_(n)—C₁-C₆-alkyl, heterocyclyl-S(O)_(n)—C₁-C₆-alkyl radicals are substituted by s residues selected from the group consisting of nitro, halogen, cyano, rhodano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(O)OR²³, C(O)N(R²³)₂, OR²³, N(R²³)₂, S(O)_(n)R²⁴, S(O)₂OR²³, S(O)₂N(R²³)₂ and R²³O—C₁-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; R²³ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl and phenyl; R²⁴ is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl and phenyl; R²⁵ is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₃-C₆-haloalkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkenylene, C₃-C₆-halocycloalkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkyl, C₁-C₆-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkyl-C₁-C₆-alkoxy-C₁-C₆-alkyl, phenyl, phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl, heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl, phenyl-N(R²³)—C₁-C₆-alkyl, heteroaryl-N(R²³)—C₁-C₆-alkyl, heterocyclyl-N(R²³)—C₁-C₆-alkyl, phenyl-S(O)_(n)—C₁-C₆-alkyl, heteroaryl-S(O)_(n)—C₁-C₆-alkyl, heterocyclyl-S(O)_(n)—C₁-C₆-alkyl, where the 15 aforementioned phenyl, phenyl-C₁-C₆-alkyl, heteroaryl, heteroaryl-C₁-C₆-alkyl, heterocyclyl, heterocyclyl-C₁-C₆-alkyl, phenyl-O—C₁-C₆-alkyl, heteroaryl-O—C₁-C₆-alkyl, heterocyclyl-O—C₁-C₆-alkyl, phenyl-N(R²³)—C₁-C₆-alkyl, heteroaryl-N(R²³)—C₁-C₆-alkyl, heterocyclyl-N(R²³)—C₁-C₆-alkyl, phenyl-S(O)_(n)—C₁-C₆-alkyl, heteroaryl-S(O)_(n)—C₁-C₆-alkyl, heterocyclyl-S(O)_(n)—C₁-C₆-alkyl radicals are substituted by s residues selected from the group consisting of nitro, halogen, cyano, rhodano, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl, C(O)OR²³, C(O)N(R²³)₂, OR²³, N(R²³)₂, S(O)_(n)R²⁴, S(O)₂OR²³, S(O)₂N(R²³)₂ and R²³O—C₁-C₆-alkyl, and where heterocyclyl bears 0, 1 or 2 oxo groups; k is 0, 1 or 2; n is 0, 1 or 2; s is 0, 1, 2, or
 3. 2. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q¹.
 3. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q².
 4. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q³.
 5. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q⁴.
 6. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R¹ is selected from the group consisting of halogen, CN, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), wherein k is 0 or
 2. 7. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R² is R^(2c)R^(2d)NC(O)NH—Z²—.
 8. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Z² in R² is a covalent bond and R^(2c) and R^(2d) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.
 9. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R³ is selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy and R^(2b)-S(O)_(k), wherein k is 0, 1 or 2 and wherein R^(2b) is selected from the group consisting of C₁-C₄-alkyl and C₁-C₄-haloalkyl.
 10. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R⁴ is hydrogen.
 11. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R⁵ is fluorine.
 12. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein R⁶ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₄-alkoxy-C₁-C₄-alkyl.
 13. A composition comprising at least one compound as claimed in claim 1, an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary, which is customary for formulating crop protection compounds.
 14. A method for controlling unwanted vegetation which comprises allowing a herbicidally effective amount of at least one compound as claimed in claim 1, an N-oxide or an agriculturally suitable salt thereof to act on plants, their seed and/or their habitat.
 15. The method of claim 14, wherein Q is Q¹.
 16. The method of claim 14, wherein Q is Q².
 17. The method of claim 14, wherein Q is Q³.
 18. The method of claim 14, wherein Q is Q⁴.
 19. The method of claim 14, wherein R¹ is selected from the group consisting of halogen, CN, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), wherein k is 0 or
 2. 20. The method of claim 14, wherein R² is R^(2c)R^(2d)NC(O)NH—Z²—.
 21. The method of claim 14, wherein Z² in R² is a covalent bond and R^(2c) and R^(2d) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄—S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy.
 22. The method of claim 14, wherein R³ is selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy and R^(2b)-S(O)_(k), wherein k is 0, 1 or 2 and wherein R^(2b) is selected from the group consisting of C₁-C₄-alkyl and C₁-C₄-haloalkyl.
 23. The method of claim 14, wherein R⁴ is hydrogen.
 24. The method of claim 14, wherein R⁵ is fluorine.
 25. The method of claim 14, wherein R⁶ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₄-alkoxy-C₁-C₄-alkyl.
 26. The compound of claim 1, an N-oxide or an agriculturally suitable salt thereof, wherein Q is Q¹; R¹ is selected from the group consisting of halogen, CN, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), wherein k is 0 or 2; R² is R^(2c)R^(2d)NC(O)NH—Z²—, where Z² in R² is a covalent bond, R^(2c) and R^(2d), independently of each other, are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₁-C₄-alkyl-C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-S(O)_(n)—C₁-C₄-alkyl, C₁-C₄-alkylamino-C₁-C₄-alkyl, C₁-C₄-dialkylamino-C₁-C₄-alkyl, C₁-C₆-cyanoalkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R³ is selected from the group consisting of hydrogen, halogen, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy and R^(2b)-S(O)_(k), wherein k is 0, 1 or 2 and wherein R^(2b) is selected from the group consisting of C₁-C₄-alkyl and C₁-C₄-haloalkyl; R⁴ is hydrogen; R⁵ is fluorine; and R⁶ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl and C₁-C₄-alkoxy-C₁-C₄-alkyl.
 27. The compound of claim 26, an N-oxide or an agriculturally suitable salt thereof, where R¹ is selected from the group consisting of halogen and C₁-C₄-alkyl; R² is R^(2c)R^(2d)NC(O)NH—Z²—, where Z² in R² is a covalent bond, R^(2c) is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, and C₁-C₄-haloalkyl; and R^(2d) is selected from the group consisting of C₁-C₄-alkyl, C₃-C₆-cycloalkyl, and C₁-C₄-haloalkyl; R³ is selected from the group consisting of halogen and C₁-C₄-haloalkyl; and R⁶ is C₁-C₄-alkyl. 